Herbicidal triazolinones

ABSTRACT

Compounds of Formula I having herbicidal utility are disclosed ##STR1## wherein the left-hand ring contains only single bonds or one bond in the ring is a double bond, and R 1 , R 2 , Q and n are defined in the text, including compositions containing such compounds and a method for controlling weeds employing such compounds.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is the international application of PCT/US94/02498 filed under 35 U.S.C. 371, which is a continuation-in-part of U.S. Ser. No. 08,038,730 filed Mar. 26, 1993 now abandoned.

BACKGROUND OF THE INVENTION

New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

U.S. Pat. No. 4,213,773 discloses herbicidal triazolinones which differ from the compounds of the present invention in that they lack a substituent on the left-hand ring.

SUMMARY OF THE INVENTION

The crop protection chemical compounds of this invention are compounds of Formula I: ##STR2## wherein the dashed line indicates that the left-hand ring contains only single bonds or one bond in the ring is a double bond;

n is 1 or 2;

R¹ is selected from the group H, halogen; hydroxy, C₁ -C₃ alkoxy; C₁ -C₃ haloalkoxy; C₂ -C₅ alkylcarbonyloxy; or C₂ -C₅ haloalkylcarbonyloxy;

R² is selected from the group H, hydroxy, and halogen; or

when R¹ and R² are bonded to the same carbon atom they can be taken together along with the carbon to which they are attached to form C═O; or

when R¹ and R² are bonded to adjacent carbon atoms they can be taken together along with the carbons to which they are attached to form ##STR3## Q is selected from the group ##STR4## R³ is selected from the group H and halogen; R⁴ is selected from the group H, C₁ -C₈ alkyl, C₁ -C₈ haloalkyl, halogen, OR⁹, S(O)_(m) R⁹, COR⁹, CO₂ R⁹, C(O)SR⁹, C(O)NR¹¹ R¹², CHO, CR⁷ ═CR⁷ CO₂ R⁹, CO₂ N═CR¹³ R¹⁴, NO₂, CN, NHSO₂ R¹⁵ and NHSO₂ NHR¹⁵ ;

m is 0, 1 or 2;

R⁵ is selected from the group C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, OCH₃, SCH₃, OCHF₂, halogen, CN and NO₂ ;

R⁶ is selected from the group H, C₁ -C₃ alkyl, C₂ -C₃ alkynyl, C₂ -C₃ haloalkynyl, CO₂ (C₁ -C₄ alkyl), and halogen;

R⁷ is independently selected from the group H, C₁ -C₃ alkyl and halogen; or

when Q is Q-2 or Q-6, R⁶ and R⁷ together with the carbon to which they are attached can be C═O;

R⁸ is selected from the group C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkoxyalkyl, C₃ -C₆ alkenyl and C₃ -C₆ alkynyl;

R⁹ is selected from the group C₁ -C₈ alkyl; C₃ -C₈ cycloalkyl; C₃ -C₈ alkenyl; C₃ -C₈ alkynyl; C₁ -C₈ haloalkyl; C₂ -C₈ alkoxyalkyl; C₂ -C₈ alkylthioalkyl; C₂ -C₈ alkylsulfinylalkyl; C₂ -C₈ alkylsulfonylalkyl; C₁ -C₈ alkylsulfonyl; phenylsulfonyl optionally substituted on the phenyl ring with halogen or C₁ -C₄ alkyl; C₄ -C₈ alkoxyalkoxyalkyl, C₄ -C₈ cycloalkylalkyl; C₄ -C₈ alkenoxyalkyl; C₄ -C₈ alkynoxyalkyl; C₆ -C₈ cycloalkoxyalkyl; C₄ -C₈ alkenyloxyalkyl; C₄ -C₈ alkynyloxyalkyl; C₃ -C₈ haloalkoxyalkyl; C₄ -C₈ haloalkenoxyalkyl; C₄ -C₈ haloalkynoxyalkyl; C₆ -C₈ cycloalkylthioalkyl; C₄ -C₈ alkenylthioalkyl; C₄ -C₈ alkynylthioalkyl; C₁ -C₄ alkyl substituted a substituent selected from phenoxy and benzyloxy, each ring optionally substituted with a substituent selected from halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; C₄ -C₈ trialkylsilylalkyl; C₃ -C₈ cyanoalkyl; C₃ -C₈ halocycloalkyl; C₃ -C₈ haloalkenyl; C₅ -C₈ alkoxyalkenyl; C₅ -C₈ haloalkoxyalkenyl; C₅ -C₈ alkylthioalkenyl; C₃ -C₈ haloalkynyl; C₅ -C₈ alkoxyalkynyl; C₅ -C₈ haloalkoxyalkynyl; C₅ -C₈ alkylthioalkynyl; C₂ -C₈ alkyl carbonyl; benzyl optionally substituted with a substituent selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; CHR¹⁶ COR¹⁰ ; CHR¹⁶ CO₂ R¹⁰ ; CHR¹⁶ P(O)(OR¹⁰)₂ ; CHR¹⁶ P(S)(OR¹⁰)₂ ; CHR¹⁶ C(O)NR¹¹ R¹² ; and CHR¹⁶ C(O)NH₂ ;

R¹⁰ is selected from the group C₁ -C₆ alkyl, C₁ -C₆ alkenyl and C₁ -C₆ alkynyl;

R¹¹ and R¹³ are independently selected from the group H and C₁ -C₄ alkyl;

R¹² and R¹⁴ are independently selected from the group C₁ -C₄ alkyl and phenyl optionally substituted with a substituent selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl;

R¹¹ and R¹² may be taken together as --(CH₂)₅ --, --(CH₂)₄ -- or --CH₂ CH₂ OCH₂ CH₂ --, each ring optionally substituted with a substituent selected from the group C₁ -C₃ alkyl, phenyl and benzyl;

R¹³ and R¹⁴ may be taken together with the carbon to which they are attached to form C₃ -C₈ cycloalkyl;

R¹⁵ is selected from the group C₁ -C₄ alkyl and C₁ -C₄ haloalkyl;

R¹⁶ is selected from the group H and C₁ -C₃ alkyl; and

W is selected from the group O and S;

provided that R¹ is other than H when the left-hand ring contains only single bonds.

In the above definitions, the terms "alkyl", "alkenyl" and "alkynyl" include straight and branched chain groups. "Halogen" means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully saturated with halogen atoms, which may be the same or different.

The bonding in compounds of Formula I is such that the left-hand ring contains single bonds, except that at most one of the bonds may be a double bond. Examples of structures of Formula I are: ##STR5##

Preferred for reasons of better biological activity and/or ease of synthesis are: Preferred 1: Compounds of Formula I wherein the left-hand ring contains only single bonds. Such compounds are compounds of Formula Ia: ##STR6## wherein n is 1 or 2;

R¹ is selected from the group halogen; hydroxy, C₁ -C₃ alkoxy; C₁ -C₃ haloalkoxy; C₂ -C₅ alkylcarbonyloxy; or C₂ -C₅ haloalkylcarbonyloxy;

R² is selected from the group H, hydroxy, and halogen; or

when R¹ and R² are bonded to the same carbon atom they can be taken together along with the carbon to which they are attached to form C═O; or

when R¹ and R² are bonded to adjacent carbon atoms they can be taken together along with the carbons to which they are attached to form ##STR7## Q is selected from the group ##STR8## R³ is selected from the group H and halogen; R⁴ is selected from the group H, C₁ -C₈ alkyl, C₁ -C₈ haloalkyl, halogen, OR⁹, S(O)_(m) R⁹, COR⁹, CO₂ R⁹, C(O)SR⁹, C(O)NR¹¹ R¹², CHO, CR⁷ ═CR⁷ CO₂ R⁹, CO₂ N═CR¹³ R¹⁴, NO₂, CN, NHSO₂ R¹⁵ and NHSO₂ NHR¹⁵ ;

m is 0, 1 or 2;

R⁵ is selected from the group C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, OCH₃, SCH₃, OCHF₂, halogen, CN and NO₂ ;

R⁶ is selected from the group H, C₁ -C₃ alkyl, C₂ -C₃ alkynyl, C₂ -C₃ haloalkynyl, CO₂ (C₁ -C₄ alkyl), and halogen;

R⁷ is independently selected from the group H, C₁ -C₃ alkyl and halogen; or

when Q is Q-2 or Q-6, R⁶ and R⁷ together with the carbon to which they are attached can be C═O;

R⁸ is selected from the group C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkoxyalkyl, C₃ -C₆ alkenyl and C₃ -C₆ alkynyl;

R⁹ is selected from the group C₁ -C₈ alkyl; C₃ -C₈ cycloalkyl; C₃ -C₈ alkenyl; C₃ -C₈ alkynyl; C₁ -C₈ haloalkyl; C₂ -C₈ alkoxyalkyl; C₂ -C₈ alkylthioalkyl; C₂ -C₈ alkylsulfmylalkyl; C₂ -C₈ alkylsulfonylalkyl; C₁ -C₈ alkylsulfonyl; phenylsulfonyl optionally substituted on the phenyl ring with halogen or C₁ -C₄ alkyl; C₄ -C₈ alkoxyalkoxyalkyl, C₄ -C₈ cycloalkylalkyl; C₄ -C₈ alkenoxyalkyl; C₄ -C₈ alkynoxyalkyl; C₆ -C₈ cycloalkoxyalkyl; C₄ -C₈ alkenyloxyalkyl; C₄ -C₈ alkynyloxyalkyl; C₃ -C₈ haloalkoxyalkyl; C₄ -C₈ haloalkenoxyalkyl; C₄ -C₈ haloalkynoxyalkyl; C₆ -C₈ cycloalkylthioalkyl; C₄ -C₈ alkenylthioalkyl; C₄ -C₈ alkynylthioalkyl; C₁ -C₄ alkyl substituted a substituent selected from phenoxy and benzyloxy, each ring optionally substituted with a substituent selected from halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; C₄ -C₈ trialkylsilylalkyl; C₃ -C₈ cyanoalkyl; C₃ -C₈ halocycloalkyl; C₃ -C₈ haloalkenyl; C₅ -C₈ alkoxyalkenyl; C₅ -C₈ haloalkoxyalkenyl; C₅ -C₈ alkylthioalkenyl; C₃ -C₈ haloalkynyl; C₅ -C₈ alkoxyalkynyl; C₅ -C₈ haloalkoxyalkynyl; C₅ -C₈ alkylthioalkynyl; C₂ -C₈ alkyl carbonyl; benzyl optionally substituted with a substituent selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; CHR¹⁶ COR¹⁰ ; CHR¹⁶ CO₂ R¹⁰ ; CHR¹⁶ P(O)(OR¹⁰)₂ ; CHR¹⁶ P(S)(OR¹⁰)₂ ; CHR¹⁶ C(O)NR¹¹ R¹² ; and CHR¹⁶ C(O)NH₂ ;

R¹⁰ is selected from the group C₁ -C₆ alkyl, C₁ -C₆ alkenyl and C₁ -C₆ alkynyl;

R¹¹ and R¹³ are independently selected from the group H and C₁ -C₄ alkyl;

R¹² and R¹⁴ are independently selected from the group C₁ -C₄ alkyl and phenyl optionally substituted with a substituent selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl;

R¹¹ and R¹² may be taken together as --(CH₂)₅ --, --(CH₂)₄ -- or --CH₂ CH₂ OCH₂ CH₂ --, each ring optionally substituted with a substituent selected from the group C₁ -C₃ alkyl, phenyl and benzyl;

R¹³ and R¹⁴ may be taken together with the carbon to which they are attached to form C₃ -C₈ cycloalkyl;

R¹⁵ is selected from the group C₁ -C₄ alkyl and C₁ -C₄ haloalkyl;

R¹⁶ is selected from the group H and C₁ -C₃ alkyl; and

W is selected from the group O and S.

Preferred 2: Compounds of Formula I wherein:

R¹ is halogen;

R² is selected from the group H, and halogen;

Q is selected from the group consisting of Q-1, Q-2 and Q-6;

R³ is halogen;

R⁵ is selected from the group C₁ -C₂ haloalkyl, OCH₃, OCHF₂, CN, NO₂, and halogen;

R⁶ is selected from the group H, C₁ -C₃ alkyl, C₂ -C₃ alkynyl, C₂ -C₃ haloalkynyl, and halogen;

R⁷ is H; and

W is O.

Preferred 3: Compounds of Preferred 2 wherein:

R⁴ is selected from the group halogen, OR⁹, S(O)_(m) R⁹, COR⁹, CO₂ R⁹, C(O)NR¹¹ R¹², CH═CHCO₂ R⁹, NHSO₂ R¹⁵ and NHSO₂ NHR¹⁵ ;

R⁵ is halogen;

R⁶ is selected from the group H and C₁ -C₃ alkyl;

R⁷ is H; and

R⁹ is selected from the group C₁ -C₈ alkyl; C₃ -C₈ cycloalkyl; C₃ -C₈ alkenyl; C₃ -C₈ alkynyl; C₁ -C₈ haloalkyl; C₂ -C₈ alkoxyalkyl; C₁ -C₄ alkyl substituted with a substituent selected from phenoxy and benzyloxy, each ring optionally substituted with a substituent selected from halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; C₃ -C₈ haloalkenyl; C₃ -C₈ haloalkynyl; C₂ -C₈ alkyl carbonyl; benzyl optionally substituted with a substituent selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; CHR¹⁶ COR¹⁰ ; CHR¹⁶ CO₂ R¹⁰ ; CHR¹⁶ P(O)(OR¹⁰)₂ ; CHR¹⁶ C(O)NR¹¹ R¹² ; and CHR¹⁶ C(O)NH₂.

Preferred compounds of the invention are:

2,5,6,7-tetrahydro-2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-6-fluoro-3H-pyrrolo 2,1-c!-1,2,4-triazol-3-one; and

5,6,7,8-tetrahydro-2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-8-chloro-1,2,4-triazolo 4,3-α!pyridin-3(2H)-one.

Compounds of General Formula I can be readily prepared by one skilled in the art by using the reactions and techniques described in Schemes 1 to 11 below. The substituents R¹ -R¹⁶, n, m, and Q for the compounds illustrated are as defined as for compounds of Formula I. Compounds prepared by Schemes 1 to 11 that include compounds numbered II to XVI are intermediates or reagents for the ultimate preparation of compounds of Formula I. Compounds of Formulae Ia-It are subsets of compounds of Formula I. In cases where the substituent of a starting material is not compatible with the reaction conditions described for any of the reaction schemes, it can be assumed that the substituent is convened to a protected form prior to the described reaction scheme and then deprotected after the reaction using commonly accepted protecting/deprotecting techniques (as an example, see T. W. Greene and P. G. M. Wuts, "Protective Groups in Organic Synthesis", 2nd Edition, John Wiley and Sons, Inc., New York, 1991). Otherwise alternative approaches known to one skilled in the art are available.

One skilled in the art will recognize that compounds of Formula I may exist as multiple stereoisomers. This invention therefore, comprises racemic mixtures, enriched mixtures, and pure enantiomers of compounds of Formula I.

The compounds of this invention are made by the following processes.

A retrosynthetic analysis of compounds of Formula Ib (compounds of Formula I wherein n is 2) is shown below (Scheme 1). The formation of ring A can be accomplished by an intramolecular cyclization between the nitrogen in ring B and the terminal double bond of triazolinone of Formula II. ##STR9##

The synthesis of the triazolinone ring B in compounds of Formula II is known in the art and can be prepared by methods such as those described in U.S. Pat. No. 4,818,275 and U.S. Pat. No. 4,818,276. Acidic condensation of α-ketoacids of Formula III and phenyl hydrazine derivatives of Formula IV gives hydrazones of Formula V. Schmidt rearrangement of the acid of Formula V with diphenylphosphoryl azide followed by a ring cyclization gives triazolinones of Formula II as shown below (Scheme 2). ##STR10##

For the synthesis of the triazolinones of Formula IIa (compounds of Formula II wherein R² is H), 2-oxo-5-hexanoic acid IIIa (compound of Formula III wherein R² is H) can be used as the starting material (Scheme 3). 2-Oxo-5-hexanoic acid can be made by hydrolysis of the methyl ester of Formula VI with base, preferably one equivalent of potassium hydroxide in an aqueous alcohol solvent. The ester of Formula VI is made from methyl pyruvate as described in J. Org. Chem., (1983), 48, 158 (scheme 3) ##STR11##

The triazolinone of Formula IIa can be made by the method described in Scheme 2. The hydrazone of Formula Va (compound of Formula V wherein R² is H) is made by treating 2-oxo-5-hexanoic acid IIIa with a phenyl hydrazine of Formula IV under acidic conditions using hydrochloric acid in an organic solvent such as ethyl or methyl alcohol at a temperature between room temperature and about 100° C. Schmidt rearrangement of hydrazone of Formula Va using an azide such as diphenylphosphoryl azide followed by intramolecular cyclization at a temperature between about 0° C. and about 100° C. affords the intermediate of Formula IIa.

Treatment of the olefin of Formula II with MCPBA (m-chloroperoxybenzoic acid) in an inert solvent such as dichloromethane at a temperature between about 0° C. and about 100° C., preferably at room temperature, gives an epoxide of Formula VII (Scheme 4). Intramolecular cyclization of the epoxide using a base such as potassium carbonate in an inert solvent such as acetonitrile or acetone gives the 6-membered ring product of Formula Ic (compound of Formula I wherein R¹ is 6-OH). Fluorination of the alcohol of Formula Ic with DAST (diethylaminosulfur trifluoride) at a temperature between about -78° C. and about 100° C. in an inert solvent such as dichloromethane gives the fluorinated product of Formula Id. ##STR12##

The alcohol of Formula Ic can also be prepared by hydroxybromination of the olefin of Formula II using N-bromosuccinimide (NBS) and water or N-bromoacetamide and water followed by cyclization of the resulting bromohydrin of Formula VIII using potassium carbonate in an inert solvent such as acetonitrile or acetone (Scheme 5). ##STR13##

Compounds of Formula Ic can also be convened to the chloro-, bromo-, and iodo-R¹ substituted bicyclic triazolinones of Formula I using methods known to those skilled in the art. The hydroxy group in compounds of Formula Ic can be acylated by known methods to prepare the alkylcarbonyloxy and haloalkylcarbonyloxy derivatives. In addition, the hydroxy or halo group can be convened by known methods to afford the R¹ ═alkoxy and haloalkoxy derivatives (March, J., Advanced Organic Chemistry, (1992), 4th Ed., John Wiley and Sons, Inc., pp 386-389). In fact all the R¹ ═OH or halogen compounds in the following Schemes can be functionalized as is known in the art to prepare the other R¹ substituted compounds. Compounds wherein R¹ and R² are taken together along with the carbon atom to which they are attached to form C═O can be prepared from the corresponding R¹ ═OH and R² ═H compounds by well-known methods for oxidizing secondary alcohols to ketones.

Compounds of Formulae Ie and If (compounds of Formula I wherein n is 1) can be prepared as illustrated in Scheme 6. Oxidative cleavage of the olefin of Formula II using sodium periodate and a catalytic amount of osmium tetroxide in an inert solvent mixture such as tetrahydrofuran (THF) and water, or using ozone in dichloromethane followed by reductive workup using dimethyl sulfide (DMS), affords the aldehyde of Formula IX. Intramolecular cyclization of the aldehyde under basic conditions using potassium carbonate or sodium hydride gives the 5-membered ring alcohol of Formula Ie. Treatment of the alcohol of Formula Ie with DAST in an inert solvent such as dichloromethane at a temperature between about -80° C. and about 60° C. produces the fluoride of Formula If. The fluoride If can also be made by direct cyclization and fluorination using DAST at a temperature range between about -100° C. and about 60° C. ##STR14##

Hydroboration of the olefin of Formula II with 9-borabicyclo 3.3.1!nonane (9-BBN) gives the alcohol of Formula X after oxidative workup (Scheme 7). Oxidation of alcohol X with oxidizing agents such as PDC (pyridinium dichlorochromate) produces the hemiaminal of Formula Ig presumably via the aldehyde intermediate of Formula XI. The fluoro compound of Formula Ih can be made by the treatment of the hemiaminal with DAST. ##STR15##

Triazolinones of Formula XII can be made from 2-oxo4-pentenoic acids and sustituted phenyl hydrazines of Formula IV by methods known to those skilled in the art and the methods taught herein (Scheme 8). The epoxide of Formula XIII can be prepared from the olefin of Formula XII using an oxidant such as MCPBA. Intramolecular cyclization of the epoxide with a base such as potassium carbonate affords the alcohol of Formula Ii. The fluoro compound of Formula Ij can be made from the alcohol using DAST at a temperature between about -70° C. and about room temperature in an inert solvent such as dichloromethane. ##STR16##

Compounds of Formula Iq can be prepared from the unsubstituted compounds of Formula XIV as illustrated in Scheme 9. Treatment of the bicyclic triazolinone of Formula XIV with N-bromosuccinimide (NBS) under allylic bromination conditions affords the mono-bromo derivative of Formula Io. One skilled in the art will recognize that bromination may also occur on Q if an electron-rich phenyl ring is present. When Q is Q-1, we have found that bromination does not occur on the phenyl ring when R³ and R⁵ are Cl and R⁴ is acetyloxy. The acetyl group can be removed by known methods, and the liberated phenolic hydroxyl group can be functionalized by known methods to prepare the desired OR⁹ group.

Hydrolysis of the bromide in hot aqueous dimethyl sulfoxide (DMSO) affords the alcohol of Formula Ip. The fluoro compound of Formula Iq can be prepared by treatment of the alcohol with diethylaminosulfur trifluoride (DAST) as described above. ##STR17##

Compounds of Formula I wherein the left-hand ring is unsaturated can be prepared by treating the hydroxy-, bromo, or chloro-substituted compound of Formula Ir with a base such as 1,8-diazabicyclo 5.4.0!undec-7-ene (DBU) as illustrated in Scheme 10. The unsaturated compound is represented by Formula Is wherein the left-hand ring contains one double bond. The hydroxy, bromo and chloro compounds of Formula Ir can be prepared by the methods described in the Schemes above. In some cases, the elimination results in a mixture of double bond isomers which can be separated by chromatography. ##STR18##

Compounds of Formula I wherein R¹ and R² are taken together along with the carbon atoms to which they are attached to form an epoxide can be prepared from the corresponding unsaturated ring compound of Formula Is by well known methods for epoxidizing double bonds, for example using MCPBA in CH₂ Cl₂.

Compounds of Formula It can be prepared as illustrated in Scheme 11. Allylic oxidation of the terminal alkene of Formula II with t-butyl hydroperoxide and catalytic selenium (IV) oxide in an inert solvent such as dichloromethane produces the allylic alcohol of Formula XV. Protection of the secondary alcohol as the t-butyldimethylsilyl (TBS) ether is accomplished using t-butylchlorodimethylsilane and a base, preferably triethylamine and catalytic 4-(dimethylamino)pyridine. The terminal olefin is converted to the primary alcohol to afford compounds of Formula XVI using 9-BBN followed by treatment with sodium perborate. Ring cyclization is accomplished using the Martin sulfurane dehydrating agent C₆ H₅ (CF₃)₂ O!₂ S(C₆ H₅)₂. Removal of the TBS group and liberation of the alcohol can be accomplished using tetrabutylammonium fluoride. The alcohol can be converted to the corresponding fluoro compound using DAST, or to other R¹ substituted compounds as described above. ##STR19##

For some compounds of Formula I wherein R² is other than hydrogen, the R² substituent is more conveniently introduced after cyclization to form the bicyclic triazolinone. This is especially the case when R¹ and R² are attached to the same carbon atom.

EXAMPLE 1 Step 1

Preparation of 2-oxo-5-hexenoic acid, 2,4-dichloro-5- (2-propynyl)oxy!-phenylhydrazone.

To a solution of 2.0 g (14.1 mmol) of methyl 2-oxo-5-hexanoate prepared as described in J. Org. Chem., (1983), 48, 158, in 2.5 mL of ethyl alcohol was added a solution of 788 mg (14.1 mmol) of potassium hydroxide in 2.5 mL of water in an ice bath. After 10 min, a mixture of 20 mL of 10% aqueous hydrochloric acid and 20 mL of ethyl alcohol and 3.25 g (14.0 mmol) of 2,4-dichloro-5- (2-propynyl)oxy!phenylhydrazine were added in sequence. The mixture was then warmed at 40° C. for 1h. The mixture was cooled to room temperature and filtered to give 3.78 g of the title product of Step 1 as a brown solid, m.p.: 152°-153° C.; ¹ H NMR (DMSO-d₆, 400 MHz) δ 12.5 (s,1H), 7.6 (s,1H), 7.4 (s,1H), 5.9 (m,1H), 4.9-5.1 (m,2H), 4.9 (s,2H) 3.7 (s,1H), 2.6 (t,2H), 2.4 (q,2H).

Step 2 Preparation of 2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-2,4-dihydro-5-(3-butenyl)-3H- 1,2,4-triazol-3-one

To a solution of 7.34 g (21.6 mmol) of 2-oxo-5-hexenoic acid, 2,4-dichloro-5- (2-propynyl)oxyl!phenylhydrazone in 100 mL of toluene was added 6.54 g (23.7 mmol) of diphenylphosphoryl azide and 3.6 mL of triethylamine (25.9 mmol) in sequence. The reaction mixture was then warmed at reflux for 1h. The mixture was cooled to room temperature and the excess toluene and triethylamine were evaporated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with 95:5 v:v mixture of dichloromethane and methanol to give 6.64 g of the title compound of Step 2 as a brown solid, m.p.: 150°-151° C.; ¹ H NMR (CDCl₃, 400 MHz) δ 11.7 (broad s,1H), 7.6 (s,1H), 7.2 (s,1H), 5.95-5.7 (m,1H), 5.2-5.0 (m,2H), 4.8 (s,2H), 2.7 (t,2) 2.6 (t,1H), 2.5 (q,2H).

Step 3 Preparation of 2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-2.4-dihydro-5-(3.4epoxybutyl)-3H- 1,2,4-triazol-3-one

To a solution of 500 mg (1.48 mmol) of 2- 2,4-dichloro-5-(2-propynyloxy)-phenyl!-2,4-dihydro-5-(3-butenyl)-3H- 1,2,4-triazol-3-one in 20 mL of dichloromethane was added 172 mg (1.63 mmol) of sodium carbonate and 970 mg of m-chloroperoxybenzoic acid (50-60%, 2.81 mmol) in an ice bath. The reaction mixture was stirred at room temperature for 24h. The mixture was filtered and the filtrate was evaporated in vacuo to give 500 mg of the title compound of Step 3 as yellow solid. The crude product was used in the following reaction without further purification. ¹ H NMR (CDCl₃, 400 MHz) δ 11.25 (s,1H), 7.55 (s,1H), 7.2 (s,1H), 4.8 (s,2H), 3.05 (m,1H), 2.8 (t,1H), 2.8 (t,2H), 2.6 (s,1H), 2.75 (d,1H), 2.2 (m,1H), 1.8 (m,1H).

Step 4 Preparation of 5,6,7,8-tetrahydro-2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-6-hydroxy- 1,2,4-triazolo 4.3-α!pyridin-3(2H)-one

A mixture of 500 mg (1.41 mmol) of 2- 2,4-dichloro-5-(2-propynyloxy)-phenyl!-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one and 563 mg (4.08 mmol) of potassium carbonate in 20 mL of acetonitrile was warmed at reflux for 2h. The mixture was cooled to room temperature and filtered. The filtrate was evaporated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 184 mg of the title product of Step 4 as a pale yellow foam, ¹ H NMR (CDCl₃, 400 MHz) δ 7.5 (s,1H), 7.15 (s,1H), 4.8 (s,2H), 4.45 (broad t,1H), 3.8 (m,2H), 3.0 (m,1H), 2.8 (m,1H), 2.6 (s,1H), 2.2 (s,1H), 2.15 (m,1H), 1.95 (m,1H).

EXAMPLE 2 Step 1 Preparation of 2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-2,4-dihydro-5-(4-bromo-3-hydroxybutyl )-3H- 1,2,4-triazol-3-one

To a solution of 200 mg (0.592 mmol) of 2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-2,4-dihydro-5-(3-butenyl)-3H-1,2,4-triazol-3-one in 1.8 mL of dimethyl sulfoxide was added 30 mL (1.67 mmol) of water and 211 mg (1.18 mmol) of N-bromosuccinimide, in sequence, at room temperature. The mixture was stirred at room temperature for 10 min. The mixture was then poured into cold water and extracted with dichloromethane. The organic layer was dried (MgSO₄) and concentrated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with a 97:3 v:v mixture of dichloromethane and methanol to give 200 mg of the title product of Step 1 as a pale yellow foam. ¹ H NMR (CDCl₃, 400 MHz) δ 11.0 (s, 1H), 7.55 (s,1H), 7.15 (s,1H), 4.8 (s,2H), 3.8 (m,1H), 3.4 (m,2H), 2.8 (m,2H), 2.6 (t,1H), 2.1-1.8 (m,2H).

Step 2 Preparation of 5,6,7,8-tetrahydro-2- 2,4,-dichloro-5-(2-propynyloxy)phenyl!- 6-hydroxy-2,4-triazolo 4,3-α!pyridin-3(2H)-one

A mixture of 200 mg (0.460 mmol) of 2- 2,4-dichloro-5-(2-propynyloxy)-phenyl!-2,4-dihydro-5-(4-bromo-3-hydroxybutyl)-3H- 1,2,4-triazol-3-one and 127 mg (0.920 mmol) of potassium carbonate in 10 mL of acetonitrile was warmed at reflux for 2h. The mixture was cooled to room temperature and filtered. The filtrate was evaporated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with a 96:4 v:v mixture of dichloromethane and methanol to give 57 mg of the title product as a pale yellow foam, The ¹ H NMR spectrum of the product was identical to that obtained for the product of Step 4 in Example 1.

EXAMPLE 3 Preparation of 5,6,7,8 tetrahydro-2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-6-fluoro-1,2,4-triazolo 4,3-α!pyridin-3(2H)-one

To a solution of 169 mg (0.477 mmol) of 5,6,7,8-tetrahydro-2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-6-hydroxy-1,2,4-triazolo 4,3-a!pyridin-3(2H)-one in 5 mL of dichloromethane was added 76 μl (0.573 mmol) of diethylaminosulfur trifluoride (DAST) at 0° C. The reaction mixture was stirred at 0° C. for 1h. The mixture was then quenched with ice and extracted with dichloromethane. The organic extracts were dried (MgSO₄), and then concentrated in vacuo to give a pale red solid. The crude product was purified by flash chromatography over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 64 mg of the title product as a pale yellow foam. ¹⁹ F NMR (CDCl₃, 400 MHz) δ-188 ppm, ¹ H NMR (CDCl₃, 400 MHz) δ 7.5 (s,1H), 7.1 (s,1H), 5.2 (m,1H), 4.8 (s,2H), 4.2-3.6 (m,2H), 3.2-3.0 (m,1H), 3.0-2.6 (m,1H), 2.5 (s,1H), 2.3-1.8 (m,2H).

EXAMPLE 4 Step 1 Preparation of 2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-2,4-dihydro-5-(3-oxo-propyl)-3H-1,2,4-triazol-3-one

To a solution of 500 mg (1.48 mmol) of 2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-2,4-dihydro-5-(3-butenyl)-3H-1,2,4-triazol-3-one in a mixture of 10 mL of tetrahydrofuran and 10 mL of water was added 696 mg (3.25 mmol) of sodium periodate and 167 mL of 0.18M aqueous solution of osmium tetroxide at room temperature. The mixture was stirred at the room temperature for 2h, and then diluted with water and extracted with ethyl acetate. The organic layer was dried (MgSO₄) and concentrated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with a 96:4 v:v mixture of dichloromethane and methanol to give 464 mg of the title product of Step 1 as a white foam. ¹ H NMR (CDCI₃, 400 MHz) δ 11.5 (broad s,1H), 9.8 (s,1H), 7.55 (s,1H), 7.2 (s,1H), 4.8 (s,2H), 2.9 (m,4H).

Step 2 Preparation of 2,5,6,7-tetrahydro-2- 2,4-dichloro-(2-propynyloxy)phenyl!-5-fluoro-3H-pyrrolo 2,1-c!-1,2,4-triazol-3-one

To a solution of 40 mg (0.117 mmol) of 2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-2,4-dihydro-5-(3-oxo-propyl)-3H-1,2,4-triazol-3-one in 5 mL of dichloromethane was added 22.7 mg (0.141 mmol) of diethylaminosulfur trifluoride at 0° C. The mixture was stirred at room temperature for 30 minutes, and then quenched with cold water and extracted with dichloromethane. The organic layer was washed with brine and water, dried (MgSO₄) and concentrated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 18 mg of 2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-2,4-dihydro-5-(3,3-difluoropropyl)-3H-1,2,4-triazol-3-one as a white foam ¹ H NMR (CDCl₃, 400 MHz) δ 12.0 (s,1H), 7.55 (s,1H), 7.2 (s,1H), 5.95 (t,1H, J=55 Hz), 4.8 (s,2H), 2.8 (t,2H), 2.6 (s,1H), 2.3 (m,2H), and 7 mg of the title product as a solid, ¹ H NMR (CDCl₃, 400 MHz) δ 7.5 (s,1H), 7.2 (s,1H), 6.4 and 6.2 (q,1H, J=60 and 5 Hz), 4.8 (s,2H), 3.15 (m,1H), 3.0-2.6 (m,3H), 2.6 (s,1H).

EXAMPLE 5 Step 1 Preparation of 5,6,7,8-tetrahydro-2-(5-acetyloxy-2,4-dichlorophenyl)-8-bromo1,2,4-triazolo 4,3-α!pyridin-3(2H)-one

To a solution of 3.55 g (10.4 mmol) of 5,6,7,8-tetrahydro-2-(5-acetyloxy-2,4-dichlorophenyl)-1,2,4-triazolo 4,3-.alpha.!pyridin-3(2H)-one in 100 mL of carbon tetrachloride was added 2.03 g (11.4 mmol) of N-bromosuccinimide at room temperature. The mixture was warmed under reflux by irradiating with a sun lamp for 3h. The mixture was cooled to room temperature and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel, eluting with a 1:1 v:v mixture of ethyl acetate and n-hexane to give 4.10 g of the title product of Step 1 as a white solid, m.p.: 75°-83° C.; ¹ H NMR (CDCl₃, 300 MHz) δ 7.6 (s,1H), 7.35 (s,1H), 5.25 (m,1H), 4.0 (m,1H), 3.6 (m,1H), 2.75 (s,3H), 2.5-1.9 (m,4H).

Step 2 Preparation of 5,6,7,8-tetrahydro-2-(2,4-dichloro-5-hydroxyphenyl)-8-hydroxy-1,2,4-triazolo 4,3-alpyridin-3(2H)-one

A mixture of 4.10 g (9.74 mmol) of 5,6,7,8-tetrahydro-2-(5-acetyloxy-2,4-dichlorophenyl)-8-bromo-1,2,4-triazolo 4,3-α!pyridin-3 (2H)-one, 50 mL of DMSO, and 50 mL of water was warmed at 90° C. for 5h. The mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with water, dried (MgSO₄) and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 1.70 g of the title product of Step 2 as a yellow oil. ¹ H NMR (CD₃ SO, 300 MHz) δ 7.65 (s,1H), 7.05 (s,1H), 5.85 (br s,1H), 4.60 (m,1H), 3.6-3.4 (m,2H), 2.2-1.8 (m,4H).

Step 3 Preparation of 5,6,7,8-tetrahydro-2- -2,4-dichloro-5-(2-propynyloxy)phenyl!-8-hydroxy-1,2,4-triazolo 4,3-α!pyridin-3(2H)-one

A mixture of 1.7 g (5.38 mmol) of 5,6,7,8-tetrahydro-2-(2,4-dichloro-5-hydroxyphenyl)-8-hydroxy-,1,2,4-triazolo 4,3-α!pyridin-3(2H)-one, 959 mL (10.7 mmol) of propargyl bromide (80% in toluene), and 1.48 g (10.7 mmol) of potassium carbonate in 20 mL of acetonitrile was warmed at reflux for 5h. The mixture was cooled to room temperature and filtered. The filtrate was evaporated under reduced pressure. The crude product was flash chromatographed over silica gel, eluting with a 97:3 v:v mixture of dichloromethane and methanol to give 1.36 g of the title product of Step 3 as a yellow solid, m.p. 168°-170° C.; ¹ H NMR (CDCl₃, 300 MHz) δ 7.55 (s,1H), 7.15 (s,1H), 4.85 (m,1H), 4.8 (d,2H), 3.8-3.6 (m,2H), 2.6 (m,1H), 2.55 (s,1H), 2.6 (m,1H), 2.55 (s,1H), 2.3-1.9 (m,4H).

Step 4 Preparation of 5,6,7,8-tetrahydro-2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-8-fluoro-1,2,4-triazolo 4,3-α!pyridin-3(2H )-one

To a solution of 300 mg (0.847 mmol) of 5,6,7,8-tetrahydro-2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-8-hydroxy-1,2,4-triazolo 4,3-α!pyridin-3(2H)-one in 10 mL of dichloromethane was added 123 mL (0.930 mmol) of diethylaminosulfur trifluoride (DAST) at -78° C. The reaction mixture was stirred at -78° C. for 4h. The mixture was warmed to room temperature, quenched with ice, and extracted with dichloromethane. The organic layers were dried (MgSO₄), and concentrated under reduced pressure. The crude product was flash chromatographed over silica gel, eluting with a 98:2 v:v mixture of dichloromethane and methanol to give 272 mg of the title product of Step 4 as a yellow solid. ¹⁹ F NMR (CDCl₃, 300 MHz) δ-172; ¹ H NMR (CDCl₃, 300 MHz) δ 7.55 (s,1H), 7.2 (s,1H), 5.6, 5.5 (2m, J=70 Hz,1H), 4.8 (s,2H), 4.0 (m,1H), 3.55 (m,1H), 2.6 (m,1H), 2.5-1.8 (m,4H).

Using the procedures outlined in Schemes 1-11, the compounds of Tables 1-6 can be prepared. ##STR20##

The following abbreviations are used in the tables which follow.

    ______________________________________                                         n = normal                                                                              Ph = phenyl                                                                              Me = methyl                                                                               i = iso                                                                              Pr = propyl                                ______________________________________                                    

                                      TABLE 1                                      __________________________________________________________________________     Compounds of Formula Ik wherein Q = Q-1; R.sup.5 = Cl                          R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                          R.sup.4                                                                               R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                           R.sup.4                                            __________________________________________________________________________     5-F H   Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    5-F H   Cl OCH(CH.sub.3)C.tbd.CH                              6-F H   Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    6-F H   Cl OCH(CH.sub.3)C.tbd.CH                              7-F H   Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    7-F H   Cl OCH(CH.sub.3)C.tbd.CH                              5-F 5-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    5-F 5-F Cl OCH(CH.sub.3)C.tbd.CH                              6-F 6-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    6-F 6-F Cl OCH(CH.sub.3)C.tbd.CH                              7-F 7-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    7-F 7-F Cl OCH(CH.sub.3)C.tbd.CH                              5-F 6-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    5-F 6-F Cl OCH(CH.sub.3)C.tbd.CH                              7-F 6-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    7-F 6-F Cl OCH(CH.sub.3)C.tbd.CH                              5-F H   F OCH.sub.2 C.tbd.CH                                                                    5-F H   F  OCH(CH.sub.3)C.tbd.CH                              6-F H   F OCH.sub.2 C.tbd.CH                                                                    6-F H   F  OCH(CH.sub.3)C.tbd.CH                              7-F H   F OCH.sub.2 C.tbd.CH                                                                    7-F H   F  OCH(CH.sub.3)C.tbd.CH                              5-F 5-F F OCH.sub.2 C.tbd.CH                                                                    5-F 5-F F  OCH(CH.sub.3)C.tbd.CH                              6-F 6-F F OCH.sub.2 C.tbd.CH                                                                    6-F 6-F F  OCH(CH.sub.3)C.tbd.CH                              7-F 7-F F OCH.sub.2 C.tbd.CH                                                                    7-F 7-F F  OCH(CH.sub.3)C.tbd.CH                              5-F 6-F F OCH.sub.2 C.tbd.CH                                                                    5-F 6-F F  OCH(CH.sub.3)C.tbd.CH                              7-F 6-F F OCH.sub.2 C.tbd.CH                                                                    7-F 6-F F  OCH(CH.sub.3)C.tbd.CH                              5-F H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-F H   Cl OCH.sub.2 CH═CH.sub.2                          6-F H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   6-F H   Cl OCH.sub.2 CH═CH.sub.2                          7-F H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   7-F H   Cl OCH.sub.2 CH═CH.sub.2                          5-F 5-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-F 5-F Cl OCH.sub.2 CH═CH.sub.2                          6-F 6-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   6-F 6-F Cl OCH.sub.2 CH═CH.sub.2                          7-F 7-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   7-F 7-F Cl OCH.sub.2 CH═CH.sub.2                          5-F 6-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-F 6-F Cl OCH.sub.2 CH═CH.sub.2                          7-F 6-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   7-F 6-F Cl OCH.sub.2 CH═CH.sub.2                          5-Cl                                                                               H   Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    5-Cl                                                                               H   Cl OCH(CH.sub.3)C.tbd.CH                              6-Cl                                                                               H   Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    6-Cl                                                                               H   Cl OCH(CH.sub.3)C.tbd.CH                              7-Cl                                                                               H   Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    7-Cl                                                                               H   Cl OCH(CH.sub.3)C.tbd.CH                              5-Cl                                                                               5-Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    5-Cl                                                                               5-Cl                                                                               Cl OCH(CH.sub.3)C.tbd.CH                              6-Cl                                                                               6-Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    6-Cl                                                                               6-Cl                                                                               Cl OCH(CH.sub.3)C.tbd.CH                              7-Cl                                                                               7-Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    7-Cl                                                                               7-Cl                                                                               Cl OCH(CH.sub.3)C.tbd.CH                              5-Cl                                                                               6-Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    5-Cl                                                                               6-Cl                                                                               Cl OCH(CH.sub.3)C.tbd.CH                              7-Cl                                                                               6-Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    7-Cl                                                                               6-Cl                                                                               Cl OCH(CH.sub.3)C.tbd.CH                              5-Cl                                                                               H   F OCH.sub.2 C.tbd.CH                                                                    5-Cl                                                                               H   F  OCH(CH.sub.3)C.tbd.CH                              6-Cl                                                                               H   F OCH.sub.2 C.tbd.CH                                                                    6-Cl                                                                               H   F  OCH(CH.sub.3)C.tbd.CH                              7-Cl                                                                               H   F OCH.sub.2 C.tbd.CH                                                                    7-Cl                                                                               H   F  OCH(CH.sub.3)C.tbd.CH                              5-Cl                                                                               5-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    5-Cl                                                                               5-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              6-Cl                                                                               6-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    6-Cl                                                                               6-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              7-Cl                                                                               7-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    7-Cl                                                                               7-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              5-Cl                                                                               6-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    5-Cl                                                                               6-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              7-Cl                                                                               6-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    7-Cl                                                                               6-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              5-Cl                                                                               H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-Cl                                                                               H   Cl OCH.sub.2 CH═CH.sub.2                          6-Cl                                                                               H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   6-Cl                                                                               H   Cl OCH.sub.2 CH═CH.sub.2                          7-Cl                                                                               H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   7-Cl                                                                               H   Cl OCH.sub.2 CH═CH.sub.2                          5-Cl                                                                               5-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-Cl                                                                               5-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          6-Cl                                                                               6-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   6-Cl                                                                               6-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          7-Cl                                                                               7-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   7-Cl                                                                               7-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          5-Cl                                                                               6-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-Cl                                                                               6-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          7-Cl                                                                               6-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   7-Cl                                                                               6-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          __________________________________________________________________________     R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.5                                                                          R.sup.4                                                                               R.sup.1                                                                             R.sup.2                                                                           R.sup.3                                                                          R.sup.5                                                                          R.sup.4                                           __________________________________________________________________________     5-F                                                                               H  Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    5-Br H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                6-F                                                                               H  Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    6-Br H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                7-F                                                                               H  Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    7-Br H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                5-F                                                                               5-F                                                                               Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    6-OMe                                                                               H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                6-F                                                                               6-F                                                                               Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    6-OCF.sub.3                                                                         H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                7-F                                                                               7-F                                                                               Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    6-MeCO                                                                              H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                5-F                                                                               6-F                                                                               Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    6-CF.sub.3 CO                                                                       H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                7-F                                                                               6-F                                                                               Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    5-F  6-OH                                                                              Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                6-carbonyl                                                                           Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    6-carbonyl                                                                             Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                               5-F                                                                               H  Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    5-F  H  F Cl                                                                               OCF.sub.2 C.tbd.CH                                6-F                                                                               H  Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    6-F  H  F Cl                                                                               OCF.sub.2 C.tbd.CH                                7-F                                                                               H  Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    7-F  H  F Cl                                                                               OCF.sub.2 C.tbd.CH                                5-F                                                                               5-F                                                                               Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    5-F  5-F                                                                               F Cl                                                                               OCF.sub.2 C.tbd.CH                                6-F                                                                               6-F                                                                               Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    6-F  6-F                                                                               F Cl                                                                               OCF.sub.2 C.tbd.CH                                7-F                                                                               7-F                                                                               Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    7-F  7-F                                                                               F Cl                                                                               OCF.sub.2 C.tbd.CH                                5-F                                                                               6-F                                                                               Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    5-F  6-F                                                                               F Cl                                                                               OCF.sub.2 C.tbd.CH                                7-F                                                                               6-F                                                                               Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    7-F  6-F                                                                               F Cl                                                                               OCF.sub.2 C.tbd.CH                                __________________________________________________________________________     Compounds of Formula II wherein Q = Q-1; R.sup.5 = Cl                          R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                          R.sup.4                                                                               R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                           R.sup.4                                            __________________________________________________________________________     5-F H   Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    5-F H   Cl OCH(CH.sub.3)C.tbd.CH                              6-F H   Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    6-F H   Cl OCH(CH.sub.3)C.tbd.CH                              7-F H   Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    7-F H   Cl OCH(CH.sub.3)C.tbd.CH                              8-F H   Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    8-F H   Cl OCH(CH.sub.3)C.tbd.CH                              5-F 5-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    5-F 5-F Cl OCH(CH.sub.3)C.tbd.CH                              6-F 6-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    6-F 6-F Cl OCH(CH.sub.3)C.tbd.CH                              7-F 7-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    7-F 7-F Cl OCH(CH.sub.3)C.tbd.CH                              8-F 8-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    8-F 8-F Cl OCH(CH.sub.3)C.tbd.CH                              5-F 6-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    5-F 6-F Cl OCH(CH.sub.3)C.tbd.CH                              6-F 7-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    6-F 7-F Cl OCH(CH.sub.3)C.tbd.CH                              8-F 7-F Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    8-F 7-F Cl OCH(CH.sub.3)C.tbd.CH                              5-F H   F OCH.sub.2 C.tbd.CH                                                                    5-F H   F  OCH(CH.sub.3)C.tbd.CH                              6-F H   F OCH.sub.2 C.tbd.CH                                                                    6-F H   F  OCH(CH.sub.3)C.tbd.CH                              7-F H   F OCH.sub.2 C.tbd.CH                                                                    7-F H   F  OCH(CH.sub.3)C.tbd.CH                              8-F H   F OCH.sub.2 C.tbd.CH                                                                    8-F H   F  OCH(CH.sub.3)C.tbd.CH                              5-F 5-F F OCH.sub.2 C.tbd.CH                                                                    5-F 5-F F  OCH(CH.sub.3)C.tbd.CH                              6-F 6-F F OCH.sub.2 C.tbd.CH                                                                    6-F 6-F F  OCH(CH.sub.3)C.tbd.CH                              7-F 7-F F OCH.sub.2 C.tbd.CH                                                                    7-F 7-F F  OCH(CH.sub.3)C.tbd.CH                              8-F 8-F F OCH.sub.2 C.tbd.CH                                                                    8-F 8-F F  OCH(CH.sub.3)C.tbd.CH                              5-F 6-F F OCH.sub.2 C.tbd.CH                                                                    5-F 6-F F  OCH(CH.sub.3)C.tbd.CH                              6-F 7-F F OCH.sub.2 C.tbd.CH                                                                    6-F 7-F F  OCH(CH.sub.3)C.tbd.CH                              8-F 7-F F OCH.sub.2 C.tbd.CH                                                                    8-F 7-F F  OCH(CH.sub.3)C.tbd.CH                              5-F H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-F H   Cl OCH.sub.2 CH.tbd.CH.sub.2                          6-F H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   6-F H   Cl OCH.sub.2 CH.tbd.CH.sub.2                          7-F H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   7-F H   Cl OCH.sub.2 CH.tbd.CH.sub.2                          8-F H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   8-F H   Cl OCH.sub.2 CH.tbd.CH.sub.2                          5-F 5-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-F 5-F Cl OCH.sub.2 CH.tbd.CH.sub.2                          6-F 6-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   6-F 6-F Cl OCH.sub.2 CH.tbd.CH.sub.2                          7-F 7-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   7-F 7-F Cl OCH.sub.2 CH.tbd.CH.sub.2                          8-F 8-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   8-F 8-F Cl OCH.sub.2 CH.tbd.CH.sub.2                          5-F 6-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-F 6-F Cl OCH.sub.2 CH.tbd.CH.sub.2                          6-F 7-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   6-F 7-F Cl OCH.sub.2 CH.tbd.CH.sub.2                          8-F 7-F Cl                                                                               OCH(CH.sub.3).sub.2                                                                   8-F 7-F Cl OCH.sub.2 CH.tbd.CH.sub.2                          5-F H   F OCH(CH.sub.3).sub.2                                                                   5-F H   F  OCH.sub.2 CH.tbd.CH.sub.2                          6-F H   F OCH(CH.sub.3).sub.2                                                                   6-F H   F  OCH.sub.2 CH.tbd.CH.sub.2                          7-F H   F OCH(CH.sub.3).sub.2                                                                   7-F H   F  OCH.sub.2 CH.tbd.CH.sub.2                          8-F H   F OCH(CH.sub.3).sub.2                                                                   8-F H   F  OCH.sub.2 CH.tbd.CH.sub.2                          5-F 5-F F OCH(CH.sub.3).sub.2                                                                   5-F 5-F F  OCH.sub.2 CH.tbd.CH.sub.2                          6-F 6-F F OCH(CH.sub.3).sub.2                                                                   6-F 6-F F  OCH.sub.2 CH.tbd.CH.sub.2                          7-F 7-F F OCH(CH.sub.3).sub.2                                                                   7-F 7-F F  OCH.sub.2 CH.tbd.CH.sub.2                          8-F 8-F F OCH(CH.sub.3).sub.2                                                                   8-F 8-F F  OCH.sub.2 CH.tbd.CH.sub.2                          5-F 6-F F OCH(CH.sub.3).sub.2                                                                   5-F 6-F F  OCH.sub.2 CH.tbd.CH.sub.2                          6-F 7-F F OCH(CH.sub.3).sub.2                                                                   6-F 7-F F  OCH.sub.2 CH.tbd.CH.sub.2                          8-F 7-F F OCH(CH.sub.3).sub.2                                                                   8-F 7-F F  OCH.sub.2 CH.tbd.CH.sub.2                          5-Cl                                                                               H   F OCH.sub.2 C.tbd.CH                                                                    5-Cl                                                                               H   F  OCH(CH.sub.3)C.tbd.CH                              6-Cl                                                                               H   F OCH.sub.2 C.tbd.CH                                                                    6-Cl                                                                               H   F  OCH(CH.sub.3)C.tbd.CH                              7-Cl                                                                               H   F OCH.sub.2 C.tbd.CH                                                                    7-Cl                                                                               H   F  OCH(CH.sub.3)C.tbd.CH                              8-Cl                                                                               H   F OCH.sub.2 C.tbd.CH                                                                    8-Cl                                                                               H   F  OCH(CH.sub.3)C.tbd.CH                              5-Cl                                                                               5-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    5-Cl                                                                               5-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              6-Cl                                                                               6-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    6-Cl                                                                               6-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              7-Cl                                                                               7-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    7-Cl                                                                               7-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              8-Cl                                                                               8-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    8-Cl                                                                               8-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              5-Cl                                                                               6-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    5-Cl                                                                               6-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              6-Cl                                                                               7-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    6-Cl                                                                               7-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              8-Cl                                                                               7-Cl                                                                               F OCH.sub.2 C.tbd.CH                                                                    8-Cl                                                                               7-Cl                                                                               F  OCH(CH.sub.3)C.tbd.CH                              5-Cl                                                                               H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-Cl                                                                               H   Cl OCH.sub.2 CH═CH.sub.2                          6-Cl                                                                               H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   6-Cl                                                                               H   Cl OCH.sub.2 CH═CH.sub.2                          7-Cl                                                                               H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   7-Cl                                                                               H   Cl OCH.sub.2 CH═CH.sub.2                          8-Cl                                                                               H   Cl                                                                               OCH(CH.sub.3).sub.2                                                                   8-Cl                                                                               H   Cl OCH.sub.2 CH═CH.sub.2                          5-Cl                                                                               5-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-Cl                                                                               5-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          6-Cl                                                                               6-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   6-Cl                                                                               6-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          7-Cl                                                                               7-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   7-Cl                                                                               7-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          8-Cl                                                                               8-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   8-Cl                                                                               8-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          5-Cl                                                                               6-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   5-Cl                                                                               6-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          6-Cl                                                                               7-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   6-Cl                                                                               7-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          8-Cl                                                                               7-Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                                                                   8-Cl                                                                               7-Cl                                                                               Cl OCH.sub.2 CH═CH.sub.2                          __________________________________________________________________________     R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.5                                                                          R.sup.4                                                                               R.sup.1                                                                             R.sup.2                                                                           R.sup.3                                                                          R.sup.5                                                                          R.sup.4                                           __________________________________________________________________________     5-F                                                                               H  Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    5-Br H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                6-F                                                                               H  Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    6-Br H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                7-F                                                                               H  Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    7-Br H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                8-Br                                                                              H  Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    8-Br H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                6-F                                                                               6-F                                                                               Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    6-OMe                                                                               H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                7-F                                                                               7-F                                                                               Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    7-OCF.sub.3                                                                         H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                5-F                                                                               6-F                                                                               Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    6-MeCO                                                                              H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                6-F                                                                               7-F                                                                               Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    6-CF.sub.3 CO                                                                       H  Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                8-F                                                                               7-F                                                                               Cl                                                                               Br                                                                               OCH.sub.2 C.tbd.CH                                                                    6-F  7-OH                                                                              Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                7-carbonyl                                                                           Cl                                                                               Cl                                                                               OCH.sub.2 C.tbd.CH                                                                    7-carbonyl                                                                             Cl                                                                               Cl                                                                               OCH(CH.sub.3).sub.2                               5-F                                                                               H  Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    5-F  H  F Cl                                                                               OCF.sub.2 C.tbd.CH                                6-F                                                                               H  Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    6-F  H  F Cl                                                                               OCF.sub.2 C.tbd.CH                                7-F                                                                               H  Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    7-F  H  F Cl                                                                               OCF.sub.2 C.tbd.CH                                8-Br                                                                              H  Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    8-Br H  F Cl                                                                               OCF.sub.2 C.tbd.CH                                6-F                                                                               6-F                                                                               Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    6-F  6-F                                                                               F Cl                                                                               OCF.sub.2 C.tbd.CH                                7-F                                                                               7-F                                                                               Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    7-F  7-F                                                                               F Cl                                                                               OCF.sub.2 C.tbd.CH                                5-F                                                                               6-F                                                                               Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    5-F  6-F                                                                               F Cl                                                                               OCF.sub.2 C.tbd.CH                                6-F                                                                               7-F                                                                               Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    6-F  7-F                                                                               F Cl                                                                               OCF.sub.2 C.tbd.CH                                8-F                                                                               7-F                                                                               Cl                                                                               Cl                                                                               OCF.sub.2 C.tbd.CH                                                                    8-F  7-F                                                                               F Cl                                                                               OCF.sub.2 C.tbd.CH                                __________________________________________________________________________

                  TABLE 2                                                          ______________________________________                                         Compounds of Formula Ik wherein Q = Q-2; R.sup.6 = H; W = O                    R.sup.1                                                                              R.sup.2 R.sup.3                                                                               R.sup.5                                                                            R.sup.7                                                                             R.sup.1                                                                              R.sup.2                                                                              R.sup.3                                                                            R.sup.5                                                                             R.sup.7                     ______________________________________                                         5-F   H       Cl     Cl  Me   5-F   H     F   Cl   Me                          6-F   H       Cl     Cl  Me   6-F   H     F   Cl   Me                          7-F   H       Cl     Cl  Me   7-F   H     F   Cl   Me                          5-F   5-F     Cl     Cl  Me   5-F   5-F   F   Cl   Me                          6-F   6-F     Cl     Cl  Me   6-F   6-F   F   Cl   Me                          7-F   7-F     Cl     Cl  Me   7-F   7-F   F   Cl   Me                          5-F   6-F     Cl     Cl  Me   5-F   6-F   F   Cl   Me                          7-F   6-F     Cl     Cl  Me   7-F   6-F   F   Cl   Me                          5-Cl  H       Cl     Cl  Me   5-Cl  H     F   Cl   Me                          6-Cl  H       Cl     Cl  Me   6-Cl  H     F   Cl   Me                          7-Cl  H       Cl     Cl  Me   7-Cl  H     F   Cl   Me                          5-Cl  5-Cl    Cl     Cl  Me   5-Cl  5-Cl  F   Cl   Me                          6-Cl  6-Cl    Cl     Cl  Me   6-Cl  6-Cl  F   Cl   Me                          7-Cl  7-Cl    Cl     Cl  Me   7-Cl  7-Cl  F   Cl   Me                          5-Cl  6-Cl    Cl     Cl  Me   5-Cl  6-Cl  F   Cl   Me                          7-Cl  6-Cl    Cl     Cl  Me   7-Cl  6-Cl  F   Cl   Me                          5-F   H       Cl     Cl  Me   5-F   H     F   Cl   Me                          6-F   H       Cl     Cl  Me   6-F   H     F   Cl   Me                          7-F   H       Cl     Cl  Me   7-F   H     F   Cl   Me                          8-F   H       Cl     Cl  Me   8-F   H     F   Cl   Me                          5-F   5-F     Cl     Cl  Me   5-F   5-F   F   Cl   Me                          6-F   6-F     Cl     Cl  Me   6-F   6-F   F   Cl   Me                          7-F   7-F     Cl     Cl  Me   7-F   7-F   F   Cl   Me                          8-F   8-F     Cl     Cl  Me   8-F   8-F   F   Cl   Me                          5-F   6-F     Cl     Cl  Me   45-F  6-F   F   Cl   Me                          6-F   7-F     Cl     Cl  Me   6-F   7-F   F   Cl   Me                          8-F   7-F     Cl     Cl  Me   8-F   7-F   F   Cl   Me                          5-Cl  H       Cl     Cl  Me   5-Cl  H     F   Cl   Me                          6-Cl  H       Cl     Cl  Me   6-Cl  H     F   Cl   Me                          7-Cl  H       Cl     Cl  Me   7-Cl  H     F   Cl   Me                          8-Cl  H       Cl     Cl  Me   8-Cl  H     F   Cl   Me                          5-Cl  5-Cl    Cl     Cl  Me   5-Cl  5-Cl  F   Cl   Me                          6-Cl  6-Cl    Cl     Cl  Me   6-Cl  6-Cl  F   Cl   Me                          7-Cl  7-Cl    Cl     Cl  Me   7-Cl  7-Cl  F   Cl   Me                          8-Cl  8-Cl    Cl     Cl  Me   8-Cl  8-Cl  F   Cl   Me                          5-Cl  6-Cl    Cl     Cl  Me   5-Cl  6-Cl  F   Cl   Me                          6-Cl  7-Cl    Cl     Cl  Me   6-Cl  7-Cl  F   Cl   Me                          8-Cl  7-Cl    Cl     Cl  Me   8-Cl  7-Cl  F   Cl   Me                          ______________________________________                                    

                                      TABLE 3                                      __________________________________________________________________________     R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.7                                                                           R.sup.8                                                                              R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.7                                                                           R.sup.8                                            __________________________________________________________________________     Compounds of the formula Ik wherein Q = Q-6; W = O; R.sup.6 = H                5-F                                                                               H  F H  CH.sub.2 C.tbd.CH                                                                    5-F                                                                               H  F H  CH(CH.sub.3)C.tbd.CH                               5-F                                                                               H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    5-F                                                                               H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               6-F                                                                               H  F H  CH.sub.2 C.tbd.CH                                                                    6-F                                                                               H  F H  CH(CH.sub.3)C.tbd.CH                               6-F                                                                               H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    6-F                                                                               H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               7-F                                                                               H  F H  CH.sub.2 C.tbd.CH                                                                    7-F                                                                               H  F H  CH(CH.sub.3)C.tbd.CH                               7-F                                                                               H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    7-F                                                                               H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               5-F                                                                               5-F                                                                               F H  CH.sub.2 C.tbd.CH                                                                    5-F                                                                               5-F                                                                               F H  CH(CH.sub.3)C.tbd.CH                               6-F                                                                               6-F                                                                               F H  CH.sub.2 C.tbd.CH                                                                    6-F                                                                               6-F                                                                               F H  CH(CH.sub.3)C.tbd.CH                               6-F                                                                               6-F                                                                               F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    6-F                                                                               6-F                                                                               F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               7-F                                                                               7-F                                                                               F H  CH.sub.2 C.tbd.CH                                                                    7-F                                                                               7-F                                                                               F H  CH(CH.sub.3)C.tbd.CH                               5-Cl                                                                              H  F H  C.sub.2 C.tbd.CH                                                                     5-Cl                                                                              H  F H  CH(CH.sub.3)C.tbd.CH                               5-Cl                                                                              H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    5-Cl                                                                              H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               6-Cl                                                                              H  F H  CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              H  F H  CH(CH.sub.3)C.tbd.CH                               6-Cl                                                                              H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               7-Cl                                                                              H  F H  CH.sub.2 C.tbd.CH                                                                    7-Cl                                                                              H  F H  CH(CH.sub.3)C.tbd.CH                               7-Cl                                                                              H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    7-Cl                                                                              H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               5-Cl                                                                              5-Cl                                                                              F H  CH.sub.2 C.tbd.CH                                                                    5-Cl                                                                              5-Cl                                                                              F H  CH(CH.sub.3)C.tbd.CH                               6-Cl                                                                              6-Cl                                                                              F H  CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              6-Cl                                                                              F H  CH(CH.sub.3)C.tbd.CH                               6-Cl                                                                              6-Cl                                                                              F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              6-Cl                                                                              F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               7-Cl                                                                              7-Cl                                                                              F H  CH.sub.2 C.tbd.CH                                                                    7-Cl                                                                              7-Cl                                                                              F H  CH(CH.sub.3)C.tbd.CH                               Compounds of Formula Il wherein Q = Q-6; W = O; R.sup.6 =H                     5-F                                                                               H  F H  CH.sub.2 C.tbd.CH                                                                    5-F                                                                               H  F H  CH(CH.sub.3)C.tbd.CH                               5-F                                                                               H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    5-F                                                                               H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               6-F                                                                               H  F H  CH.sub.2 C.tbd.CH                                                                    6-F                                                                               H  F H  CH(CH.sub.3)C.tbd.CH                               6-F                                                                               H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    6-F                                                                               H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               7-F                                                                               H  F H  CH.sub.2 C.tbd.CH                                                                    7-F                                                                               H  F H  CH(CH.sub.3)C.tbd.CH                               7-F                                                                               H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    7-F                                                                               H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               8-F                                                                               H  F H  CH.sub.2 C.tbd.CH                                                                    8-F                                                                               H  F H  CH(CH.sub.3)C.tbd.CH                               8-F                                                                               H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    8-F                                                                               H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               5-F                                                                               5-F                                                                               F H  CH.sub.2 C.tbd.CH                                                                    5-F                                                                               5-F                                                                               F H  CH(CH.sub.3)C.tbd.CH                               6-F                                                                               6-F                                                                               F H  CH.sub.2 C.tbd.CH                                                                    6-F                                                                               6-F                                                                               F H  CH(CH.sub.3)C.tbd.CH                               7-F                                                                               7-F                                                                               F H  CH.sub.2 C.tbd.CH                                                                    7-F                                                                               7-F                                                                               F H  CH(CH.sub.3)C.tbd.CH                               7-F                                                                               7-F                                                                               F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    7-F                                                                               7-F                                                                               F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               8-F                                                                               8-F                                                                               F H  CH.sub.2 C.tbd.CH                                                                    8-F                                                                               8-F                                                                               F H  CH(CH.sub.3)C.tbd.CH                               5-Cl                                                                              H  F H  CH.sub.2 C.tbd.CH                                                                    5-Cl                                                                              H  F H  CH(CH.sub.3)C.tbd.CH                               5-Cl                                                                              H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    5-Cl                                                                              H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               6-Cl                                                                              H  F H  CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              H  F H  CH(CH.sub.3)C.tbd.CH                               6-Cl                                                                              H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               7-Cl                                                                              H  F H  CH.sub.2 C.tbd.CH                                                                    7-Cl                                                                              H  F H  CH(CH.sub.3)C.tbd.CH                               7-Cl                                                                              H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    7-Cl                                                                              H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               8-Cl                                                                              H  F H  CH.sub.2 C.tbd.CH                                                                    8-Cl                                                                              H  F H  CH(CH.sub.3)C.tbd.CH                               8-Cl                                                                              H  F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    8-Cl                                                                              H  F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               5-Cl                                                                              5-Cl                                                                              F H  CH.sub.2 C.tbd.CH                                                                    5-Cl                                                                              5-Cl                                                                              F H  CH(CH.sub.3)C.tbd.CH                               6-Cl                                                                              6-Cl                                                                              F H  CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              6-Cl                                                                              F H  CH(CH.sub.3)C.tbd.CH                               7-Cl                                                                              7-Cl                                                                              F H  CH.sub.2 C.tbd.CH                                                                    7-Cl                                                                              7-Cl                                                                              F H  CH(CH.sub.3)C.tbd.CH                               7-Cl                                                                              7-Cl                                                                              F CH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                    7-Cl                                                                              7-Cl                                                                              F CH.sub.3                                                                          CH(CH.sub.3)C.tbd.CH                               8-Cl                                                                              8-Cl                                                                              F H  CH.sub.2 C.tbd.CH                                                                    8-Cl                                                                              8-Cl                                                                              F H  CH(CH.sub.3)C.tbd.CH                               __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________     R.sup.3                                                                          R.sup.4                                                                             R.sup.3                                                                          R.sup.4  R.sup.3                                                                          R.sup.4  R.sup.3                                                                          R.sup.4                                         __________________________________________________________________________     Compounds of Formula Ik wherein Q = Q-1; R.sup.1 = 6-F; R.sup.2 = H;           R.sup.5 = Cl                                                                   Cl                                                                               H    Cl                                                                               SCH.sub.2 C.tbd.CH                                                                      Cl                                                                               CH═CHCO.sub.2 (i-Pr)                                                                Cl                                                                               OCH.sub.2 OCH.sub.3                             F H    F SCH.sub.2 C.tbd.CH                                                                      F CH═CHCO.sub.2 (i-Pr)                                                                F OCH.sub.2 OCH.sub.3                             Cl                                                                               O-(n-Pr)                                                                            Cl                                                                               SCH(CH.sub.3)C.tbd.CH                                                                   Cl                                                                               OCH.sub.2 CO.sub.2 (i-Pr)                                                               Cl                                                                               SCH.sub.2 CO.sub.2 Et                           F O-(n-Pr)                                                                            F SCH(CH.sub.3)C.tbd.CH                                                                   F OCH.sub.2 CO.sub.2 (i-Pr)                                                               F SCH.sub.2 CO.sub.2 Et                           Cl                                                                               OCH.sub.2 CF.sub.3                                                                  Cl                                                                               NHSO.sub.2 CH.sub.3                                                                     Cl                                                                               OCH.sub.2 OPh                                                                           Cl                                                                               OCH.sub.2 CO(i-Pr)                              Cl                                                                               CO.sub.2 (i-Pr)                                                                     F NHSO.sub.2 CH.sub.3                                                                     F OCH.sub.2 OPh                                                                           F OCH.sub.2 CO(i-Pr)                              F CO.sub.2 (i-Pr)                                                                     Cl                                                                               OCH.sub.2 CO.sub.2 (n-pentyl)                                                           F OCH.sub.2 CO.sub.2 (n-pentyl)                              Compounds of Formula Il wherein Q = Q-1; R.sup.1 = 6-F; R.sup.2 = H;           R.sup.5 = Cl                                                                   Cl                                                                               H    Cl                                                                               SCH.sub.2 C.tbd.CH                                                                      Cl                                                                               CH═CHCO.sub.2 (i-Pr)                                                                Cl                                                                               OCH.sub.2 OCH.sub.3                             F H    F SCH.sub.2 C.tbd.CH                                                                      F CH═CHCO.sub.2 (i-Pr)                                                                F OCH.sub.2 OCH.sub.3                             Cl                                                                               O-(n-Pr)                                                                            Cl                                                                               SCH(CH.sub.3)C.tbd.CH                                                                   Cl                                                                               OCH.sub.2 CO.sub.2 (i-Pr)                                                               Cl                                                                               SCH.sub.2 CO.sub.2 Et                           F O-(n-Pr)                                                                            F SCH(CH.sub.3)C.tbd.CH                                                                   F OCH.sub.2 CO.sub.2 (i-Pr)                                                               F SCH.sub.2 CO.sub.2 Et                           Cl                                                                               OCH.sub.2 CF.sub.3                                                                  Cl                                                                               NHSO.sub.2 CH.sub.3                                                                     Cl                                                                               OCH.sub.2 OPh                                                                           Cl                                                                               OCH.sub.2 CO(i-Pr)                              Cl                                                                               CO.sub.2 (i-Pr)                                                                     F NHSO.sub.2 CH.sub.3                                                                     F OCH.sub.2 OPh                                                                           F OCH.sub.2 CO(i-Pr)                              F CO.sub.2 (i-Pr)                                                                     Cl                                                                               OCH.sub.2 CO.sub.2 (n-pentyl)                                                           F OCH.sub.2 CO.sub.2 (n-pentyl)                              __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________     Compounds of Formula Ik wherein Q = Q-4; W = S;                                R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                          R.sup.9                                                                              R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.9                                                                              R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.9                                      __________________________________________________________________________     5-F                                                                              H F CH.sub.2 C.tbd.CH                                                                    5-Cl                                                                              H  F CH.sub.2 C.tbd.CH                                                                    6-F                                                                               6-F                                                                               F CH.sub.2 C.tbd.CH                            5-F                                                                              H F CH.sub.2 C.tbd.CH                                                                    5-Cl                                                                              H  F CH.sub.2 C.tbd.CH                                                                    6-F                                                                               6-F                                                                               F CH.sub.2 C.tbd.CH                            6-F                                                                              H F CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              H  F CH.sub.2 C.tbd.CH                                                                    7-F                                                                               7-F                                                                               F CH.sub.2 C.tbd.CH                            6-F                                                                              H F CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              H  F CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              6-Cl                                                                              F CH.sub.2 C.tbd.CH                            7-F                                                                              H F CH.sub.2 C.tbd.CH                                                                    7-Cl                                                                              H  F CH.sub.2 C.tbd.CH                                                                    6-Cl                                                                              6-Cl                                                                              F CH.sub.2 C.tbd.CH                            7-F                                                                              H F CH.sub.2 C.tbd.CH                                                                    7-Cl                                                                              H  F CH.sub.2 C.tbd.CH                                                                    7-Cl                                                                              7-Cl                                                                              F CH.sub.2 C.tbd.CH                            5-F                                                                              5-F                                                                              F CH.sub.2 C.tbd.CH                                                                    5-Cl                                                                              5-Cl                                                                              F CH.sub.2 C.tbd.CH                                          __________________________________________________________________________     R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                           R.sup.9  R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                           R.sup.9                                           __________________________________________________________________________     5-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    5-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              5-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    5-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              6-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    6-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              6-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    6-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              7-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    7-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              7-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    7-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              5-F                                                                               5-F                                                                               F  CH(CH.sub.3)C.tbd.CH                                                                    5-Cl                                                                               5-Cl                                                                               F  CH(CH.sub.3)C.tbd.CH                              6-F                                                                               6-F                                                                               F  CH(CH.sub.3)C.tbd.CH                                                                    6-Cl                                                                               6-Cl                                                                               F  CH(CH.sub.3)C.tbd.CH                              6-F                                                                               6-F                                                                               F  CH(CH.sub.3)C.tbd.CH                                                                    6-Cl                                                                               6-Cl                                                                               F  CH(CH.sub.3)C.tbd.CH                              7-F                                                                               7-F                                                                               F  CH(CH.sub.3)C.tbd.CH                                                                    7-Cl                                                                               7-Cl                                                                               F  CH(CH.sub.3)C.tbd.CH                              __________________________________________________________________________     Compounds of the Formula II wherein Q = Q-4; W = S;                            R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                          R.sup.9                                                                              R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.9                                                                              R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.9                                      __________________________________________________________________________     5-F                                                                              H F CH.sub.2 C═CH                                                                    5-Cl                                                                              H  F CH.sub.2 C.tbd.CH                                                                    7-F                                                                               7-F                                                                               F CH.sub.2 C.tbd.CH                            5-F                                                                              H F CH.sub.2 C═CH                                                                    5-Cl                                                                              H  F CH.sub.2 C═CH                                                                    7-F                                                                               7-F                                                                               F CH.sub.2 C═CH                            6-F                                                                              H F CH.sub.2 C═CH                                                                    6-Cl                                                                              H  F CH.sub.2 C═CH                                                                    8-F                                                                               8-F                                                                               F CH.sub.2 C═CH                            6-F                                                                              H F CH.sub.2 C═CH                                                                    6-Cl                                                                              H  F CH.sub.2 C═CH                                                                    7-Cl                                                                              7-Cl                                                                              F CH.sub.2 C═CH                            7-F                                                                              H F CH.sub.2 C═CH                                                                    7-Cl                                                                              H  F CH.sub.2 C═CH                                                                    7-Cl                                                                              7-Cl                                                                              F CH.sub.2 C═CH                            7-F                                                                              H F CH.sub.2 C═CH                                                                    7-Cl                                                                              H  F CH.sub.2 C═CH                                                                    8-Cl                                                                              8-C                                                                               F CH.sub.2 C═CH                            8-F                                                                              H F CH.sub.2 C═CH                                                                    8-Cl                                                                              H  F CH.sub.2 C═CH                                                                    6-F                                                                               6-F                                                                               F CH.sub.2 C═CH                            8-F                                                                              H F CH.sub.2 C═CH                                                                    8-Cl                                                                              H  F CH.sub.2 C═CH                                                                    6-Cl                                                                              6-Cl                                                                              F CH.sub.2 C═CH                            5-F                                                                              4-F                                                                              F CH.sub.2 C═CH                                                                    5-Cl                                                                              5-Cl                                                                              F CH.sub.2 C═CH                                          __________________________________________________________________________     R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                           R.sup.9  R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                           R.sup.9                                           __________________________________________________________________________     5-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    5-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              5-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    5-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              6-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    6-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              6-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    6-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              7-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    7-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              7-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    7-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              8-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    8-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              8-F                                                                               H  F  CH(CH.sub.3)C.tbd.CH                                                                    8-Cl                                                                               H   F  CH(CH.sub.3)C.tbd.CH                              5-F                                                                               5-F                                                                               F  CH(CH.sub.3)C.tbd.CH                                                                    5-Cl                                                                               5-Cl                                                                               F  CH(CH.sub.3)C.tbd.CH                              6-F                                                                               6-F                                                                               F  CH(CH.sub.3)C.tbd.CH                                                                    6-Cl                                                                               6-Cl                                                                               F  CH(CH.sub.3)C.tbd.CH                              7-F                                                                               7-F                                                                               F  CH(CH.sub.3)C.tbd.CH                                                                    7-Cl                                                                               7-Cl                                                                               F  CH(CH.sub.3)C.tbd.CH                              7-F                                                                               7-F                                                                               F  CH(CH.sub.3)C.tbd.CH                                                                    7-Cl                                                                               7-Cl                                                                               F  CH(CH.sub.3)C.tbd.CH                              8-F                                                                               8-F                                                                               F  CH(CH.sub.3)C.tbd.CH                                                                    8-Cl                                                                               8-Cl                                                                               F  CH(CH.sub.3)C.tbd.CH                              __________________________________________________________________________

                  TABLE 6                                                          ______________________________________                                         R.sup.1                                                                            R.sup.2                                                                              R.sup.3                                                                              R.sup.1                                                                             R.sup.2                                                                            R.sup.3                                                                            R.sup.1                                                                             R.sup.2                                                                             R.sup.3                                                                            R.sup.1                                                                              R.sup.2                                                                             R.sup.3                  ______________________________________                                         Compounds of Formula Ik wherein Q = Q-5; R.sup.6 = R.sup.7 = CF.sub.3 ;        5-F H     F     6-F  6-F F   7-Cl H    F   5-F   5-F  F                        5-F H     Cl    6-F  6-F Cl  7-Cl H    Cl  5-F   5-F  Cl                       6-F H     F     7-F  7-F F   5-Cl 5-Cl F   6-Cl  H    F                        6-F H     Cl    7-F  7-F Cl  5-Cl 5-Cl Cl  6-Cl  H    Cl                       7-F H     F     5-Cl H   F   6-Cl 6-Cl F   7-Cl  7-Cl F                        7-F H     Cl    5-Cl H   Cl  6-Cl 6-Cl Cl  7-Cl  7-Cl Cl                       Compounds of Formula Il wherein Q = Q-5; R.sup.6 = R.sup.7 = CF.sub.3 ;        5-F H     F     5-F  5-F F   5-Cl 5-Cl F   6-F   6-F  F                        5-F H     Cl    5-F  5-F Cl  5-Cl 5-Cl Cl  6-F   6-F  Cl                       6-F H     F     7-F  7-F F   8-Cl H    F   7-Cl  H    F                        6-F H     Cl    7-F  7-F Cl  8-Cl H    Cl  7-Cl  H    Cl                       7-F H     F     7-F  8-F F   6-Cl 6-Cl F   8-CL  8-Fl F                        7-F H     Cl    8-F  8-F Cl  6-Cl 6-Cl Cl  8-Cl  8-Cl Cl                       8-F H     F     6-Cl H   F   7-Cl 7-Cl F                                       8-F H     Cl    6-Cl H   Cl  7-Cl 7-Cl Cl                                      ______________________________________                                    

Formulation/Utility

The compounds of this invention are useful as herbicides in agriculture. Typically, such compound(s) can be formulated in an effective amount with conventional additives including a carrier therefor (comprising a surfactant and/or a solid or liquid diluent) and applied by known methods to the locus to be protected.

Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent. Useful formulations include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent.

    ______________________________________                                                        Weight Percent                                                                 Active                                                                         Ingredient                                                                            Diluent   Surfactant                                     ______________________________________                                         Wettable Powders 25-90     0-74     1-10                                       Oil Suspensions, Emulsions,                                                                      5-50    40-95     0-15                                       Solutions, (including Emulsifiable                                             Concentrates)                                                                  Dusts             1-25    70-99     0-5                                        Granules and Pellets                                                                            0.01-99     5-99.99                                                                               0-15                                       High Strength Compositrons                                                                      90-99     0-10     0-2                                        ______________________________________                                    

Typical solid diluents are described in Watkins, et al., Handbook of insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, (1950). McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, (1964), list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.

Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill. Water-dispersible granules can be produced by agglomerating a free powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., (1988), pp 251-259. Suspensions are prepared by wet-milling; see, for example, U.S. Pat. No. 3,060,084. Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, (1963), pp 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 3,246,493.

For further information regarding the art of formulation, see U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, (1961), pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, (1989).

In the following Examples, all percentages are by weight and all formulations are worked up in conventional ways. The compound number refers to the compound in Index Table A hereinafter.

    ______________________________________                                         Example A                                                                      High Strength Concentrate                                                      Compound 12           98.5%                                                    silica aerogel        0.5%                                                     synthetic amorphous fine silica                                                                      1.0%.                                                    Example B                                                                      Wettable Powder                                                                Compound 12           65.0%                                                    dodecylphenol polyethylene glycol ether                                                              2.0%                                                     sodium ligninsulfonate                                                                               4.0%                                                     sodium silicoaluminate                                                                               6.0%                                                     montmorillonite (calcined)                                                                           23.0%.                                                   Example C                                                                      Granule                                                                        Compound 12           10.0%                                                    attapulgite granules (low volatile                                                                   90.0%.                                                   matter, 0.71/0.30 mm; U.S.S. No.                                               25-50 sieves)                                                                  Example D                                                                      Extruded Pellet                                                                Compound 12           25.0%                                                    anhydrous sodium sulfate                                                                             10.0%                                                    crude calcium ligninsulfonate                                                                        5.0%                                                     sodium alkylnaphthalenesulfonate                                                                     1.0%                                                     calcium/magnesium bentonite                                                                          59.0%.                                                   ______________________________________                                    

The compounds of the present invention are highly active preemergent and/or postemergent herbicides and/or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards and highway and railroad structures. Some of the compounds are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include but are not limited to barley, cotton, wheat, corn, soybeans, rice, citrus, peanut, and plantation crops such as sugarcane, coffee, banana, oil palm, rubber, grapes, fruit trees, nut trees, turf, pineapple and loblolly pine. The compounds of the instant invention are particularly useful on plantation crops such as sugarcane, coffee, banana, oil palm, rubber, grapes, fruit trees, nut trees, turf, pineapple and loblolly pine. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.

Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. A mixture of one or more of the following herbicides with a compound of this invention can be particularly useful for weed control: acetochlor, acifluorfen, acrolein, 2-propenal, alachlor, ametryn, amidosulfuron, ammonium sulfamate, amitrole, anilofos, asulam, atrazine, barban, benefin, bensulfuron methyl, bensulide, bentazon, benzofluor, benzoylprop, bifenox, bromacil, bromoxynil, bromoxynil heptanoate, bromoxynil octanoate, butachlor, buthidazole, butralin, butylate, cacodylic acid, 2-chloro-N,N-di-2-propenyl-acetamide, 2-chloroallyl diethyldithiocarbamate, chloramben, chlorbromuron, chloridazon, chlorimuron ethyl, chlormethoxynil, chlornitrofen, chloroxuron, chlorpropham, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clomazone, cloproxydim, clopyralid, calcium salt of methylarsonic acid, cyanazine, cycloate, cycluron, cyperquat, cyprazine, cyprazole, cypromid, dalapon, dazomet, dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate, desmedipham, desmetryn, dicamba, dichlobenil, dichlorprop, diclofop, diethatyl, difenzoquat, diflufenican, dimepiperate, dinitramine, dinoseb, diphenamid, dipropetryn, diquat, diuron, 2-methyl-4,6-dinitrophenol, disodium salt of methylarsonic acid, dymron, endothall, S-ethyl dipropylcarbamothioate, esprocarb, ethalfluralin, ethametsulfuron methyl, ethofumesate, fenac, fenoxaprop, fenuron, salt of fenuron and trichloroacetic acid, flamprop, fluazifop, fluazifop-P, fluchloralin, flumesulam, flumipropyn, fluomemron, fluorochloridone, fluorodifen, fluoroglycofen, flupoxam, fluridone, fluroxypyr, fluzasulfuron, fomesafen, fosamine, glyphosate, glyphosate salts, haloxyfop, hexaflurate, hexazinone, imazamethabenz, imazapyr, imazaquin, imazamethabenz methyl, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, karbutilate, lactofen, lenacil, linuron, metobenzuron, metsulfuron methyl, methylarsonic acid, monoammonium salt of methylarsonic acid, (4-chloro-2-methylphenoxy)acetic acid, S,S'-dimethyl-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothioate, mecoprop, mefenacet, mefluidide, methalpropalin, methabenzthiazuron, metham, methazole, methoxuron, metolachlor, metribuzin, 1,2-dihydropyridazine-3,6-dione, molinate, monolinuron, monuron, monuron salt and trichloroacetic acid, monosodium salt of methylarsonic acid, napropamide, naptalam, neburon, nicosulfuron, nitralin, nitrofen, nitrofluorfen, norea, norflurazon, oryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, perfluidone, phenmedipham, picloram, 5- 2-chloro-4-(trifluoromethyl)phenoxy!-2-nitroacetophenone oxime-O-acetic acid methyl ester, pretilachlor, primisulfuron, procyazine, profluralin, prometon, prometryn, pronamide, propachlor, propanil, propazine, propham, prosulfalin, prynachlor, pyrazolate, pyrazon, pyrazosulfuron ethyl, quinchlorac, quizalofop ethyl, rimsulfuron, secbumeton, sethoxydim, siduron, simazine, 1-(α,α-dimethylbenzyl)-3-(4-methylphenyl)urea, sulfometuron methyl, trichloroacetic acid, tebuthiuron, terbacil, terbuchlor, terbuthylazine, terbutol, terbutryn, thifensulfuron methyl, thiobencarb, tri-allate, trialkoxydim, triasulfuron, tribenuron methyl, triclopyr, tridiphane, trifluralin, trimeturon, (2,4-dichlorophenoxy)acetic acid, 4-(2,4-dichlorophenoxy)butanoic acid, vernolate, and xylachlor.

In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management.

A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of a compound(s) of this invention is applied at rates from about 0.005 to 5.0 kg/ha with a preferred rate range of 0.010 to 2.0 kg/ha. One skilled in the art can easily determine application rates necessary for the desired level of weed control.

The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A and B for compound descriptions.

    __________________________________________________________________________     Index Table A                                                                   ##STR21##                                                                     Compound of Formula Im wherein:                                                Cmpd No.                                                                             R.sup.1                                                                              R.sup.2                                                                           R.sup.3                                                                           R.sup.4   R.sup.5                                                                           m.p. (°C.).sup.1,2                       __________________________________________________________________________      1    6-OH  H  Cl OCH.sub.2 C CH                                                                           Cl oil                                              2    8-OH  H  Cl OCH.sub.2 C CH                                                                           Cl 168-170                                          3    8-Br  H  Cl OC(O)Me   Cl  75-83                                           4    8-Br  H  Cl OC(O)Me   Cl  77-82                                           5    8-Br  H  Cl OS(O).sub.2 (4-CH.sub.3 Ph)                                                              Cl oil                                              6    8-Br  8-Br                                                                              Cl OS(O).sub.2 (4-CH.sub.3 Ph)                                                              Cl 161-162 d                                        7    6-Br  H  Cl OCH.sub.2 C CH                                                                           Cl oil                                              8    6-F   H  Cl OCH.sub.2 C CH                                                                           Cl oil                                              9    6-(O)    Cl OCH.sub.2 C CH                                                                           Cl oil                                             10    6-OC(O)Me                                                                            H  Cl OCH.sub.2 C CH                                                                           Cl oil                                             11    8-F   H  Cl OCH.sub.2 C CH                                                                           Cl oil                                             12    8-Cl  H  Cl OCH.sub.2 C CH                                                                           Cl oil                                             13    7-OH  8-OH                                                                              Cl OS(O).sub.2 (4-CH.sub.3 Ph)                                                              Cl glass                                           14    8-OC(O)Me                                                                            H  Cl OCH.sub.2 C CH                                                                           Cl oil                                             15    7-OH  8-OH                                                                              Cl OCH.sub.2 C CH                                                                           Cl oil                                             16    8-OH  H  Cl OS(O).sub.2 (4-CH.sub.3 Ph)                                                              Cl oil                                             17    8-(O)    Cl OS(O).sub.2 (4-CH.sub.3 Ph)                                                              Cl oil                                             18    8-(O)    Cl OCH.sub.2 C CH                                                                           Cl oil                                             19    7-OH  H  Cl OCH.sub.2 C CH                                                                           Cl oil                                             20    8-F   H  Cl OCH.sub.3 Cl 148-151                                         21    6-OH  H  H  H         F  oil                                             22    6-Cl  H  Cl OCH.sub.2 C CH                                                                           Cl oil                                             23    8-OH  H  Cl OCH.sub.3 Cl 245-247                                         24    6-OH  H  Cl OCH.sub.2 C CH                                                                           Cl 186-187                                         25    6-F   H  Cl OCH.sub.2 C CH                                                                           Cl oil                                             26    6-Cl  H  Cl OCH.sub.2 C CH                                                                           Cl oil                                             27    7-Cl  H  Cl OCH.sub.2 C CH                                                                           Cl oil                                             28    7-F   H  Cl OCH.sub.2 C CH                                                                           Cl oil                                             29    8-OH  H  Cl OH        Cl 238-240 d                                       30    8-Br  H  Cl OH        Cl 187-190                                         31    7-OH  8-OH                                                                              Cl OH        Cl 215-218                                         32    8-OH  H  Cl OH        Cl oil                                             33    8-(O)    Cl OH        Cl oil                                             __________________________________________________________________________

    ______________________________________                                         Index Table B                                                                   ##STR22##                                                                     Compound of Formula In wherein:                                                Cmpd No.                                                                               R.sup.1                                                                               R.sup.3                                                                               R.sup.4     R.sup.5                                                                             m.p. (°C.).sup.1                 ______________________________________                                         36      H      Cl     OS(O).sub.2 (4-CH.sub.3 Ph)                                                                Cl   oil                                     37      H      Cl     OH          Cl   oil                                     38      Br     Cl     OH          Cl   246-247                                 39      Br     Cl     OC(O)Me     Cl   oil                                      ##STR23##                                                                      ##STR24##                                                                     ______________________________________                                          .sup.1 .sup.1 H NMR data for oils and glass in Index Table C.                  .sup.2 d = decomposed                                                    

                  INDEX TABLE C                                                    ______________________________________                                               .sup.1 HNMR Data                                                         Cmpd  (solvent = CDCl.sub.3 unless otherwise indicated,                        No.   in ppm downfield from tetramethylsilane)                                 ______________________________________                                          1    7.55(s, 1H), 7.2(s, 1H), 4.8(s, 2H), 4.4(m, 1H), 3.75(m, 2H), 3.2              (s, 1H), 3.0(m, 1H), 2.75(m, 1H), 2.6(s, 1H), 2.1(m, 1H), 1.9                  (m, 1H).                                                                  5    7.78(d, 2H), 7.55(s, 1H), 7.50(s, 1H), 7.35(d, 2H), 5.27(t, 1H),               4.0(m, 1H), 3.61(m, 1H), 2.45(s, 3H), 2.1-2.5(m, 4H).                     7    7.6(s, 1H), 7.1(s, 1H), 4.8(q, 2H), 4.6(m, 1H), 4.0(m, 1H), 3.8                (m, 1H), 3.2(m, 1H), 3.0(m, 1H), 2.6(m, 1H), 2.4(m, 2H).                  8    7.55(s, 1H), 7.2(s, 1H), 5.4, 5.2(2m, 1H), 4.8(d, 2H), 4.1(m,                  1H), 3.8-3.6(4d, 1H), 2.95(m, 2H), 2.6(m, 1H), 2.5(m, 1H), 2.0                 (m, 1H).                                                                  9    7.55(s, 1H), 7.2(s, 1H), 4.8(s, 2H), 4.4(s, 2H), 3.15(m, 2H), 2.8              (m, 2H), 2.6(s, 1H).                                                     10    7.55(s, 1H), 7.2(s, 1H), 5.4(m, 1H), 4.8(s, 2H), 3.95(m, 1H), 3.8              (dd, 1H), 2.9(m, 2H), 2.6(s, 1H), 2.3(m, 1H), 2.1(s, 3H), 2.0                  (m, 1H).                                                                 11    7.55(s, 1H), 7.2(s, 1H), 5.6, 5.5(2m, 1H), 4.8(s, 2H), 4.0(m,                  1H), 3.55(m, 1H), 2.6(m, 1H), 2.5-1.8(m, 4H).                            12    7.55(s, 1H), 7.2(s, 1H), 5.15(t, 1H), 4.8(s, 2H), 3.95(m, 1H),                 3.6(m, 1H), 2.6(m, 1H), 2.5-2.0(m, 4H).                                  13    7.81(d, 2H), 7.63(s, 1H), 7.50(s, 1H), 7.35(d, 2H), 4.62(dd, 1H),              4.15(m, 1H), 3.89(m, 1H), 3.71(m, 1H), 3.55(d, 1H), 2.77(d,                    1H), 2.46(s, 3H), 2.36(m, 1H), 2.1(m, 1H).                               14    7.55(s, 1H), 7.15(m, 1H), 5.95(m, 1H), 4.8(s, 2H), 3.85(m, 1H),                3.6(m, 1H), 2.6(s, 1H), 2.2-2.0(m, 4H), 2.15(s, 3H).                     15    (solvent = (CD.sub.3).sub.2 SO) 7.85(s, 1H), 7.35(s, 1H), 6.13(d,              1H),                                                                           5.44(d, 1H), 4.97(d, 2H), 4.35(m, 1H), 3.95(m, 1H), 3.70(t,                    1H), 3.65(m, 1H), 3.5(m, 1H), 2.15(m, 1H), 1.9(m, 1H).                   16    7.78(d, 2H), 7.60(s, 1H), 7.50(s, 1H), 7.34(d, 2H), 4.85(m, 1H),               2.78(d, 1H), 2.45(s, 3H), 2.25(m, 1H), 2.0(m, 3H).                       17    7.77(d, 2H), 7.60(s, 1H), 7.53(s, 1H), 7.30(d, 2H), 4.00(m, 2H),               2.86(m, 2H), 2.46(s, 3H), 2.42(m, 2H).                                   18    (solvent = (CD.sub.3).sub.2 SO) 7.92(s, 1H), 7.42(s, 1H), 4.98(d,              2H),                                                                           3.8(t, 2H), 3.70(t, 1H), 2.75(t, 2H), 2.25(m, 2H).                       19    7.54(s, 1H), 7.16(s, 1H), 4.77(d, 2H), 4.40(m, 1H), 3.75-3.90                  (m, 2H), 3.6(t, 1H), 2.9-3.0(m, 2H), 2.6(m, 1H), 2.0-2.2(m,                    2H).                                                                     21    7.9(m, 2H), 7.1(m, 2H), 4.5(m, 1H), 3.8(m, 2H), 3.0(m, 1H),                    2.8(m, 1H), 2.2(m, 1H), 1.9(m, 1H), 1.6(hr s, 1H).                       22    7.55(s, 1H), 7.2(s, 1H), 4.8(s, 2H), 4.6(m, 1H), 4.0(m, 2H), 3.15              (m, 1H), 2.9(m, 1H), 2.6(m, 1H), 2.3(m, 2H).                             25    7.55(s, 1H), 7.2(s, 1H), 6.3, 6.15(2t, 1H), 4.8(d, 2H), 3.0(m,                 1H), 2.7(m, 1H), 2.6(m, 1H), 2.5(m, 1H), 2.2-1.8(m, 3H).                 26    7.55(s, 1H), 7.2(s, 1H), 6.2(m, 1H), 4.8(t, 2H), 3.0(m, 1H), 2.8               (m, 1H), 2.6(m, 1H), 2.6-2.0(m, 4H)                                      27    7.55(s, 1H), 7.2(s, 1H), 4.8(d, 2H), 4.6(m, 1H), 4.0-3.8(m, 2H),               3.2(m, 2H), 2.65(m, 1H), 2.6(m, 1H), 2.4(m, 1H).                         28    7.6(s, 1H), 7.2(s, 1H), 5.4, 5.2(2q, 1H), 4.8(d, 2H), 4.0-3.75                 (m, 2H), 3.3-2.8(m, 2H), 2.6(m, 1H), 2.5(m, 1H), 2.2-2.0(m,                    1H).                                                                     32    (solvent = (CD.sub.3).sub.2 SO) 10.9(s, 1H), 7.65(s, 1H), 7.02(s,              1H), 5.22                                                                      (d, 1H), 4.17(m, 1H), 3.55(m, 2H), 2.80(m, 1H), 2.59(dd, 1H),                  1.95(m, 2H).                                                             33    (solvent = (CD.sub.3).sub.2 SO) 11.1(s, 1H), 7.75(s, 1H), 7.09(s,              1H), 3.78                                                                      (t, 2H), 2.74(d, 2H), 2.25(m, 2H).                                       34    7.55(s, 1H), 7.2(s, 1H), 6.4, 6.2(2d, 1H), 4.8(s, 2H), 3.2-2.6(m,              4H), 2.6(s, 1H).                                                         35    7.55(s, 1H), 7.2(s, 1H), 5.2(d, 1H), 4.8(d, 2H), 4.0(m, 2H), 2.8               (m, 2H), 2.6(m, 1H).                                                     36    7.80(d, 2H), 7.62(s, 1H), 7.48(s, 1H), 7.34(d, 2H), 6.43(m, 2H),               3.89(t, 2H), 2.69(dt, 2H), 2.45(s, 3H).                                  37    7.46(s, 1H), 7.10(s, 1H), 6.4(m, 2H), 3.89(t, 2H), 2.65(m, 2H).          39    7.6(s, 1H), 7.35(s, 1H), 6.7(t, 1H), 3.9(t, 2H), 2.7(q, 2H), 2.35              (s, 3H).                                                                 ______________________________________                                    

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Gatlum aparine), blackgrass (Alopecurus myosuroides), cheatgrass (Bromus secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), downy brome (Bromus rectorurn), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

                  TABLE A                                                          ______________________________________                                                COMPOUND                                                                Rate 400 g/ha                                                                           8     10    11  12  14  20  21  22  23  35  36                                                     38                                                ______________________________________                                         POSTEMERGENCE                                                                  Barley   9     6     7   8   8   9   0   6   2   4   4                                                      2                                                                              Barnyardgrass 10 3 10 10 10 10 0 10 5 9 3 2                                    Bedstraw 10 5 10 9 8 9 2 10 2 9 1 1                                            Blackgrass 10 4 10 9 9 10 0 10 2 9 3 2                                         Chickweed 10 4 10 2 4 3 0 9 0 5 1 2                                            Cocklebur 9 7 9 8 8 8 0 10 4 7 4 2                                             Corn 9 5 8 8 9 9 0 7 3 5 3 2                                                   Cotton 10 10 10 10 10 10 0 10 9 10 9 9                                         Crabgrass 10 4 9 8 8 10 0 9 3 8 4 2                                            Downy brome 9 4 8 6 5 9 0 8 1 5 2 1                                            Giant foxtail 10 3 9 9 9 9 0 9 3 8 3 2                                         Lambsquarter 10 7 10 10 10 10 0 10 9 10 6 4                                    Morningglory 10 9 10 10 10 10 0 10 7 9 4 2                                     Nutsedge 10 8 -- 5 6 10 0 6 1 5 0 1                                            Rape 10 6 10 10 9 9 0 10 7 8 5 1                                               Rice 10 5 9 8 8 9 0 9 5 6 3 3                                                  Sorghum 10 4 9 9 9 10 0 9 3 6 3 3                                              Soybean 9 7 9 9 9 9 1 9 5 9 5 3                                                Sugar beet 10 7 10 10 10 10 0 10 7 10 6 3                                      Velvetleaf 10 10 10 10 10 10 0 10 9 10 8 2                                     Wheat 9 6 9 9 8 9 0 6 2 5 4 1                                                  Wild 10 10 10 10 10 10 2 10 9 10 3 2                                           buckwheat                                                                      Wild oat 10 5 9 8 9 9 0 9 1 8 3 2                 PREMERGENCE                                                                    Barley   6     0     8   8   7   8   0   2   2   0   0                                                      0                                                                              Barnyardgrass 10 7 10 9 10 10 0 9 7 4 0 0                                      Bedstraw 10 3 10 7 9 7 0 10 3 9 2 0                                            Blackgrass 8 1 10 9 9 10 0 9 2 6 0 0                                           Chickweed 10 2 10 4 8 4 0 10 0 2 0 0                                           Cocklebur 10 0 10 5 9 10 0 7 3 2 0 2                                           Corn 8 3 7 5 10 7 0 9 2 3 0 0                                                  Cotton 9 0 10 7 9 8 0 9 3 1 0 0                                                Crabgrass 10 1 10 10 10 10 0 10 4 10 0 2                                       Downy brome 10 0 9 7 10 10 0 8 3 5 1 0                                         Giant foxtail 10 4 10 9 10 10 0 9 8 10 0 0                                     Lambsquarter 10 8 10 10 10 10 3 10 10 10 4 0                                   1                                                                              Morningglory 10 1 10 10 10 7 0 10 5 10 0 5                                     Nutsedge 3 2 3 1 8 4 0 2 8 1 3 0                                               Rape 10 2 10 10 10 10 0 10 8 8 1 0                                             Rice 9 5 9 5 8 9 0 5 3 2 0 0                                                   Sorghum 10 2 10 10 9 10 0 7 2 4 0 0                                            Soybean 9 2 10 7 9 9 0 10 4 1 0 3                                              Sugar beet 10 4 10 10 10 10 0 10 9 10 3 0                                      Velvetleaf 10 10 10 10 10 10 0 10 9 10 0 0                                     Wheat 7 0 10 9 9 9 0 4 6 1 0 0                                                 Wild 10 2 10 10 10 10 0 10 8 10 0 0                                            buckwheat                                                                      Wild oat 9 0 10 10 9 10 0 9 6 6 0 0               ______________________________________                                                 COMPOUND                                                               Rate 200 g/ha                                                                            6             24    40                                               ______________________________________                                         POSTEMERGENCE                                                                  Barley    2             3     0                                                Barnyardgrass                                                                            2             3     1                                                Bedstraw  1             3     2                                                Blackgrass                                                                               2             4     3                                                Chickweed 1             2     0                                                Cocklebur 2             3     2                                                Corn      2             2     1                                                Cotton    9             9     2                                                Crabgrass 5             4     1                                                Downy brome                                                                              2             3     0                                                Giant foxtail                                                                            3             3     2                                                Lambsquarter                                                                             4             4     3                                                Morningglory                                                                             3             5     1                                                Nutsedge  1             1     --                                               Rape      3             3     0                                                Rice      3             3     1                                                Sorghum   3             4     1                                                Soybean   3             2     3                                                Sugar beet                                                                               5             8     0                                                Velvetleaf                                                                               6             7     4                                                Wheat     5             4     0                                                Wild buckwheat                                                                           4             3     3                                                Wild oat  3             3     2                                                PREEMERGENCE                                                                   Barley    1             0     0                                                Barnyardgrass                                                                            0             0     0                                                Bedstraw  2             0     0                                                Blackgrass                                                                               1             0     2                                                Chickweed 0             0     0                                                Cocklebur 0             0     0                                                Corn      0             0     0                                                Cotton    0             0     0                                                Crabgrass 3             0     0                                                Downy brome                                                                              1             0     2                                                Giant foxtail                                                                            0             0     0                                                Lambsquarter                                                                             0             0     0                                                Morningglory                                                                             0             0     0                                                Nutsedge  0             0     0                                                Rape      1             0     0                                                Rice      0             0     0                                                Sorghum   0             0     0                                                Soybean   0             0     0                                                Sugar beet                                                                               0             0     0                                                Velvetleaf                                                                               3             0     0                                                Wheat     0             0     0                                                Wild buckwheat                                                                           2             0     0                                                Wild oat  0             0     0                                                ______________________________________                                                    COMPOUND                                                            Rate 50 g/ha 6     24          37  40                                          ______________________________________                                         POSTEMERGENCE                                                                  Barley       1     3           1   0                                           Barnyardgrass                                                                               2     3           2   1                                           Bedstraw     1     3           0   2                                           Blackgrass   1     3           2   2                                           Chickweed    1     0           0   0                                           Cocklebur    1     2           0   2                                           Corn         2     2           1   1                                           Cotton       5     9           4   2                                           Crabgrass    3     4           2   1                                           Downy brome  0     2           0   0                                           Giant foxtail                                                                               2     2           2   1                                           Lambsquarter 2     3           0   3                                           Morningglory 2     2           0   1                                           Nutsedge     1     0           0   --                                          Rape         2     0           0   0                                           Rice         2     3           0   1                                           Sorghum      2     3           2   1                                           Soybean      3     2           1   2                                           Sugar beet   4     7           2   0                                           Velvetleaf   --    7           0   3                                           Wheat        4     3           2   0                                           Wild buckwheat                                                                              3     2           0   1                                           Wild oat     3     3           2   2                                           PREEMERGENCE                                                                   Barley       1     0           0   0                                           Barnyardgrass                                                                               0     0           0   0                                           Bedstraw     0     0           0   0                                           Blackgrass   1     0           0   0                                           Chickweed    0     0           0   0                                           Cocklebur    0     0           0   0                                           Corn         0     0           2   0                                           Cotton       0     0           0   0                                           Crabgrass    0     0           3   0                                           Downy brome  0     0           0   0                                           Giant foxtail                                                                               0     0           2   0                                           Lambsquarter 0     0           0   0                                           Morningglory 0     0           0   0                                           Nutsedge     0     0           0   0                                           Rape         1     0           2   0                                           Rice         0     0           0   0                                           Sorghum      0     0           0   0                                           Soybean      0     0           0   0                                           Sugar beet   0     0           0   0                                           Velvetleaf   0     0           0   0                                           Wheat        0     0           0   0                                           Wild buckwheat                                                                              0     0           0   0                                           Wild oat     0     0           0   0                                           ______________________________________                                         Rate     COMPOUND                                                              100 g/ha                                                                              8     9     10  11  12  14  20  21  22  23  35                                                     36  38                                              ______________________________________                                         Barley 7     4     3   7   5   5   7   0   4   1   4                                                      3   1                                                                          Barnyard-                                                                          9 2 2 9 9 9 9 0 9 3 9 3 1                                                  grass                                                                          Bedstraw                                                                           9 7 4 10 9 6 9 0 9 2 6 1 1                                                 Blackgrass                                                                         9 4 4 9 8 4 7 0 5 1 4 2 1                                                  Chick-                                                                             9 5 4 7 1 3 3 0 6 0 4 1 1                                                  weed                                                                           Cocklebur                                                                          9 4 6 10 7 7 7 0 7 3 7 3 1                                                 Corn                                                                               8 2 2 7 5 5 5 0 6 3 2 3 1                                                  Cotton                                                                             10 9 9 10 10 10 10 0 10 9 9 9 6                                            Crabgrass                                                                          7 3 3 8 8 3 6 0 8 3 4 3 2                                                  Downy                                                                              7 3 3 8 5 3 7 0 3 1 4 2                                                    brome                                                                          Giant                                                                              6 3 3 9 8 5 7 0 9 3 6 3 1                                                  foxtail                                                                        Lambs-                                                                             10 4 6 10 10 10 9 0 10 8 10 4 2                                            quarter                                                                        Morning-                                                                           9 7 9 10 10 9 10 0 9 7 8 4 2                                               glory                                                                          Nutsedge                                                                           10 1 4 4 3 2 2 0 3 1 2 0 1                                                 Rape                                                                               9 4 6 9 9 8 8 0 10 5 7 3 1                                                 Rice                                                                               8 5 4 9 7 5 7 0 9 3 4 3 2                                                  Sorghum                                                                            9 4 3 8 7 8 9 0 9 3 4 3 3                                                  Soybean                                                                            9 6 6 8 8 9 8 0 9 4 5 3 2                                                  Sugar beet                                                                         10 7 7 10 8 10 10 0 9 6 8 4 2                                              Velvetleaf                                                                         10 7 7 10 9 9 10 0 10 5 8 5 1                                              Wheat                                                                              9 5 3 9 7 7 8 0 6 1 5 4 1                                                  Wild                                                                               10 8 7 10 10 10 9 0 10 7 9 2 2                                             buckwheat                                                                      Wild oat                                                                           8 3 3 8 4 6 8 0 8 0 5 2 1                       PREEMERGENCE                                                                   Barley 6     1     0   6   2   4   4   0   1   0   0                                                      0   0                                                                          Barnyard-                                                                          9 0 1 10 8 9 10 0 8 2 1 0 0                                                grass                                                                          Bedstraw                                                                           9 1 2 10 10 0 3 0 8 0 1 0 0                                                Blackgrass                                                                         7 2 1 9 7 5 9 0 8 0 3 1 0                                                  Chick-                                                                             10 0 0 9 2 0 2 0 10 0 3 0 0                                                weed                                                                           Cocklebur                                                                          3 0 0 6 2 4 5 0 5 2 0 0 1                                                  Corn                                                                               7 0 0 6 4 6 3 0 5 0 1 0 0                                                  Cotton                                                                             10 0 -- 7 0 2 1 0 2 0 0 0 0                                                Crab-                                                                              10 0 -- 10 8 9 10 0 10 2 6 0 0                                             grass                                                                          Downy                                                                              6 2 0 6 7 5 8 0 6 1 3 0 0                                                  brome                                                                          Giant                                                                              9 0 0 10 8 9 10 0 9 8 6 0 0                                                foxtail                                                                        Lambs-                                                                             10 6 4 10 10 10 10 0 10 9 10 2 0                                           quarter                                                                        Morning-                                                                           10 0 0 8 3 6 6 0 10 4 10 0 0                                               glory                                                                          Nutsedge                                                                           1 -- 0 2 0 1 2 0 1 0 0 0 0                                                 Rape                                                                               8 1 2 10 5 8 9 0 9 3 2 1 0                                                 Rice                                                                               7 0 2 8 4 6 7 0 3 2 0 0 0                                                  Sorghum                                                                            9 0 0 4 3 7 5 0 3 0 0 0 0                                                  Soybean                                                                            10 0 2 8 4 9 6 0 9 2 0 0 1                                                 Sugar beet                                                                         10 6 2 10 10 10 10 0 10 7 10 2 0                                           Velvetleaf                                                                         10 4 5 10 9 10 10 0 10 9 9 0 0                                             Wheat                                                                              7 1 0 7 1 7 5 0 2 1 2 0 0                                                  Wild                                                                               10 1 0 10 8 10 9 0 6 3 7 0 0                                               buckwheat                                                                      Wild oat                                                                           8 0 0 9 5 7 7 0 9 2 3 0 0                       ______________________________________                                                   COMPOUND                                                             Rate 20 g/ha                                                                             9                                                                    ______________________________________                                         POSTEMERGENCE                                                                  Barley    3                                                                    Barnyardgrass                                                                            2                                                                    Bedstraw  5                                                                    Blackgrass                                                                               1                                                                    Chickweed 3                                                                    Cocklebur 4                                                                    Corn      2                                                                    Cotton    7                                                                    Crabgrass 4                                                                    Downy brome                                                                              1                                                                    Giant foxtail                                                                            4                                                                    Lambsquarter                                                                             4                                                                    Morningglory                                                                             6                                                                    Nutsedge  --                                                                   Rape      3                                                                    Rice      4                                                                    Sorghum   3                                                                    Soybean   5                                                                    Sugar beet                                                                               4                                                                    Velvetleaf                                                                               5                                                                    Wheat     4                                                                    Wild buckwheat                                                                           7                                                                    Wild oat  3                                                                    PREEMERGENCE                                                                   Barley    0                                                                    Barnyardgrass                                                                            0                                                                    Bedstraw  1                                                                    Blackgrass                                                                               0                                                                    Chickweed 0                                                                    Cocklebur 0                                                                    Corn      0                                                                    Cotton    0                                                                    Crabgrass 0                                                                    Downy brome                                                                              0                                                                    Giant foxtail                                                                            0                                                                    Lambsquarter                                                                             0                                                                    Morningglory                                                                             0                                                                    Nutsedge  0                                                                    Rape      1                                                                    Rice      0                                                                    Sorghum   0                                                                    Soybean   0                                                                    Sugar beet                                                                               2                                                                    Velvetleaf                                                                               3                                                                    Wheat     0                                                                    Wild buckwheat                                                                           1                                                                    Wild oat  0                                                                    ______________________________________                                                   COMPOUND                                                             Rate 10 g/ha                                                                             37                                                                   ______________________________________                                         POSTEMERGENCE                                                                  Barley    0                                                                    Barnyardgrass                                                                            0                                                                    Bedstraw  0                                                                    Blackgrass                                                                               0                                                                    Chickweed 0                                                                    Cocklebur 0                                                                    Corn      0                                                                    Cotton    0                                                                    Crabgrass 1                                                                    Downy brome                                                                              0                                                                    Giant foxtail                                                                            --                                                                   Lambsquarter                                                                             0                                                                    Morningglory                                                                             --                                                                   Nutsedge  0                                                                    Rape      0                                                                    Rice      0                                                                    Sorghum   0                                                                    Soybean   0                                                                    Sugar beet                                                                               0                                                                    Velvetleaf                                                                               0                                                                    Wheat     1                                                                    Wild buckwheat                                                                           0                                                                    Wild oat  1                                                                    PREEMERGENCE                                                                   Barley    0                                                                    Barnyardgrass                                                                            0                                                                    Bedstraw  0                                                                    Blackgrass                                                                               0                                                                    Chickweed 0                                                                    Cocklebur 0                                                                    Corn      0                                                                    Cotton    0                                                                    Crabgrass 0                                                                    Downy brome                                                                              0                                                                    Giant foxtail                                                                            0                                                                    Lambsquarter                                                                             0                                                                    Morningglory                                                                             0                                                                    Nutsedge  0                                                                    Rape      0                                                                    Rice      0                                                                    Sorghum   0                                                                    Soybean   0                                                                    Sugar beet                                                                               0                                                                    Velvetleaf                                                                               0                                                                    Wheat     0                                                                    Wild buckwheat                                                                           0                                                                    Wild oat  0                                                                    ______________________________________                                    

TEST B

Seeds of barnyardgrass (Echinochloa crus-galli), cheatgrass (Bromus secalinus), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberii), morningglory (Ipomoea spp.), sorghum (Sorghum bicolor), velvetleaf (Abutilon theophrasti), and wild oat (Avenafatua) were planted into a sandy loam soil and treated preemergence, or with a soil drench(PDRN), with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated postemergence, or sprayed to runoff(STRO), with test chemicals. Plants ranged in height from two to eighteen cm and were in the two to three leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table B, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test results.

                  TABLE B                                                          ______________________________________                                                   COMPOUND                                                             Rate 2000 g/ha                                                                           7                                                                    ______________________________________                                         PDRN                                                                           Barnyardgrass                                                                            0                                                                    Cocklebur 0                                                                    Crabgrass 0                                                                    Downy brome                                                                              0                                                                    Giant foxtail                                                                            0                                                                    Morningglory                                                                             0                                                                    Sorghum   0                                                                    Velvetleaf                                                                               0                                                                    Wild oats 0                                                                    STRO                                                                           Barnyardgrass                                                                            1                                                                    Cocklebur 0                                                                    Crabgrass 1                                                                    Downy brome                                                                              1                                                                    Giant foxtail                                                                            2                                                                    Morningglory                                                                             1                                                                    Sorghum   1                                                                    Velvetleaf                                                                               5                                                                    Wild oats 2                                                                    ______________________________________                                                    COMPOUND                                                            Rate 800 g/ha                                                                               3     4           13  30                                          ______________________________________                                         PREEMERGENCE                                                                   Barnyardgrass                                                                               0     0           0   0                                           Cocklebur    0     0           0   0                                           Crabgrass    0     0           0   0                                           Downy brome  0     0           0   0                                           Giant foxtail                                                                               0     0           0   0                                           Morningglory 0     0           0   0                                           Sorghum      0     0           0   0                                           Velvetleaf   0     0           0   0                                           Wild oats    0     0           0   0                                           POSTEMERGENCE                                                                  Barnyardgrass                                                                               2     2           1   2                                           Cocklebur    2     1           0   1                                           Crabgrass    1     1           1   1                                           Downy brome  1     1           0   1                                           Giant foxtail                                                                               1     1           0   2                                           Morningglory 0     0           1   0                                           Sorghum      3     2           1   2                                           Velvetleaf   3     2           1   2                                           Wild oats    1     1           0   2                                           ______________________________________                                    

TEST C

The compounds evaluated in this test were formulated in a non- phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted of barnyardgrass (Echinochloa crus-galli), barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), johnsongrass (Sorghum halpense), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), sorghum (Sorghum bicolor), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua). All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the flood test consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa), barnyardgrass (Echinochloa crus-galli) and Late watergrass (Echinocloa oryzicola) grown to the 1 and 2 leaf stage for testing.

All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response ratings, summarized in Table C, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

                  TABLE C                                                          ______________________________________                                                   COMPOUND                                                             Rate 125 g/ha                                                                              11     12          14   20                                         ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri  65     35          45   85                                        Barnyardgrass                                                                              100     95          85   80                                        Blackgrass  100     40          50   45                                        Chickweed    85     45          30   35                                        Cocklebur    55     65          65   70                                        Corn         50     65          35   50                                        Cotton      100    100         100  100                                        Crabgrass    35     65          80   90                                        Downy Brome  90     55          45   90                                        Duck salad   35     20          50   90                                        Galium      100     60          65   70                                        Giant foxtail                                                                               95     95          80   95                                        Italn. Rygrass                                                                             100     55          75  100                                        Johnsongrass                                                                               100     95         100  100                                        Lambsquarters                                                                              100    100         100   95                                        Morningglory                                                                               100    100         100   95                                        Rape        100    100         100  100                                        Redroot Pigweed                                                                            100     90         100  100                                        Rice Japonica                                                                               95     80          95   90                                        Soybean      85     75          90   90                                        Speedwell   100    100         100  --                                         Sugar beet  100    100         100  100                                        Umbrella sedge                                                                             100     60          45   90                                        Velvetleaf  100    100         100  100                                        Watergrass 2                                                                               100    100          90   95                                        Wheat       100     35          45  100                                        Wild buckwheat                                                                             100    100         100  100                                        Wild oat    100     60          65   95                                        2 Leaf BYG  100    100         100   95                                        PREEMERGENCE                                                                   Barley Igri  70     15          25   55                                        Barnyardgrass                                                                               95    100         100  100                                        Blackgrass  100     80          60   95                                        Chickweed   100     0           25   60                                        Cocklebur    35     0           85   65                                        Corn         65     0           85   70                                        Cotton       95     0           90   85                                        Crabgrass   100     95         100  100                                        Downy Brome  90     01          30   55                                        Galium      100     80          90   30                                        Giant foxtail                                                                              100    100         100  100                                        Italn. Rygrass                                                                             100     90          80  100                                        Johnsongrass                                                                               100     95         100  100                                        Lambsquarters                                                                              100    100         100  100                                        Morningglory                                                                                85     30          65   95                                        Rape        100     95          95  100                                        Redroot Pigweed                                                                            100    100          90  100                                        Soybean      60     25          40   90                                        Speedwell   100     55         100  100                                        Sugar beet  100    100         100  100                                        Velvetleaf  100    100         100  100                                        Wheat        80     45          35   95                                        Wild buckwheat                                                                             100    100         100  100                                        Wild oat    100     55          60   70                                        POSTEMERGENCE                                                                  Barley Igri  65     35          45   85                                        Barnyardgrass                                                                              100     95          85   80                                        Blackgrass  100     40          50   45                                        Chickweed    85     45          30   35                                        Cocklebur    55     65          65   70                                        Corn         50     65          35   50                                        Cotton      100    100         100  100                                        Crabgrass    35     65          80   90                                        Downy Brome  90     55          45   90                                        Duck salad   35     20          50   90                                        Galium      100     60          65   70                                        Giant foxtail                                                                               95     90          80   95                                        Italn. Rygrass                                                                             100     55          75  100                                        Johnsongrass                                                                               100     95         100  100                                        Lambsquarters                                                                              100    100         100   95                                        Morningglory                                                                               100    100         100   95                                        Rape        100    100         100  100                                        Redroot Pigweed                                                                            100     90         100  100                                        Rice Japonica                                                                               95     80          95   90                                        Soybean      85     75          90   90                                        Speedwell   100    100         100  --                                         Sugar beet  100    100         100  100                                        Umbrella sedge                                                                             100     60          45   90                                        Velvetleaf  100    100         100  100                                        Watergrass 2                                                                               100    100          90   95                                        Wheat       100     35          45  100                                        Wild buckwheat                                                                             100    100         100  100                                        Wild oat    100     60          65   95                                        2 Leaf BYG  100    100         100   95                                        PREEMERGENCE                                                                   Barley Igri  70     15          25   55                                        Barnyardgrass                                                                               95    100         100  100                                        Blackgrass  100     80          60   95                                        Chickweed   100     0           25   60                                        Cocklebur    35     0           85   65                                        Corn         65     0           85   70                                        Cotton       95     0           90   85                                        Crabgrass   100     95         100  100                                        Downy Brome  90     10          30   55                                        Galium      100     80          90   30                                        Giant foxtail                                                                              100    100         100  100                                        Italn. Rygrass                                                                             100     90          80  100                                        Johnsongrass                                                                               100     95         100  100                                        Lambsquarters                                                                              100    100         100  100                                        Morningglory                                                                                85     30          65   95                                        Rape        100     95          95  100                                        Redroot Pigweed                                                                            100    100          90  100                                        Soybean      60     25          40   90                                        Speedwell   100     55         100  100                                        Sugar beet  100    100         100  100                                        Velvetleaf  100    100         100  100                                        Wheat        80     45          35   95                                        Wild buckwheat                                                                             100    100         100  100                                        Wild oat    100     55          60   70                                        ______________________________________                                                 COMPOUND                                                               Rate 62 g/ha                                                                             11        12     14     20   22                                      ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri                                                                              65        35     45     85    0                                      Barnyardgrass                                                                            100       65     45     80   95                                      Blackgrass                                                                               95        40     50     35   65                                      Chickweed 80        30     30     20   95                                      Cocklebur 50        45     45     45   95                                      Corn      35        30     35     50   60                                      Cotton    100       100    100    100  100                                     Crabgrass 35        35     25     70   35                                      Downy Brome                                                                              85        50     45     40   65                                      Duck salad                                                                               30         0      0     85   60                                      Galium    100       55     65     20   100                                     Giant foxtail                                                                            95        90     45     95   100                                     Italn. Rygrass                                                                           95        50     60     90   75                                      Johnsongrass                                                                             90        95     90     100  100                                     Lambsquarters                                                                            100       100    100    95   100                                     Morningglory                                                                             100       95     100    95   95                                      Rape      100       100    95     80   100                                     Redroot Pigweed                                                                          100       90     100    100  100                                     Rice Japonica                                                                            95        70     80     80   75                                      Soybean   80        75     80     85   75                                      Speedwell 100       95     100    --   100                                     Sugar beet                                                                               100       100    100    100  100                                     Umbrella sedge                                                                           95        30     30     90   80                                      Velvetleaf                                                                               100       90     100    100  100                                     Watergrass 2                                                                             100       100    75     95   95                                      Wheat     95        30     45     95   65                                      Wild buckwheat                                                                           100       95     100    95   100                                     Wild oat  95        60     30     85   85                                      2 Leaf BYG                                                                               100       100    85     90   95                                      PREEMERGENCE                                                                   Barley Igri                                                                              50         0      0     35   25                                      Barnyardgrass                                                                            95        85     80     90   95                                      Blackgrass                                                                               100       45     30     80   65                                      Chickweed 40         0      0     30   95                                      Cocklebur 10         0     30     50   30                                      Corn      50         0     65     50   65                                      Cotton    55         0     60     75    0                                      Crabgrass 100       85     90     100  100                                     Downy Brome                                                                              70         0     30     55   35                                      Galium    80        40     10     10   100                                     Giant foxtail                                                                            100       95     50     100  90                                      Italn. Rygrass                                                                           95        65     40     95   90                                      Johnsongrass                                                                             100       95     100    95   95                                      Lambsquarters                                                                            100       90     100    100  100                                     Morningglory                                                                             40         0     30      0   80                                      Rape      100       24      0     80   80                                      Redroot Pigweed                                                                          100       100    75     100  100                                     Soybean   --        25     35     70   95                                      Speedwell 100       40     95     100  100                                     Sugar beet                                                                               100        0     100    100  95                                      Velvetleaf                                                                               100       100    100    100  100                                     Wheat     65         0      0     90   40                                      Wild buckwheat                                                                           100       45     95     95   100                                     Wild oat  85        10      0     70   70                                      ______________________________________                                                 COMPOUND                                                               Rate 31 g/ha                                                                             11        12     14     20   22                                      ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri                                                                              55        35     40     50    0                                      Barnyardgrass                                                                            85        25     40     80   65                                      Blackgrass                                                                               50        35     35     25   60                                      Chickweed 65.230    30     20     80                                           Cocklebur  0        40     40     45   50                                      Corn       0        30     25     50   35                                      Cotton    100       100    100    100  100                                     Crabgrass  0        30     25     65   10                                      Downy Brome                                                                              75        40     35     40   35                                      Duck salad                                                                                0         0      0      0   10                                      Galium    95        45     45     15   100                                     Giant foxtail                                                                            65        70     45     95   55                                      Italn. Rygrass                                                                           85        45     45     80   55                                      Johnsongrass                                                                             60        90     90     95   95                                      Lambsquarters                                                                            100       95     100    95   100                                     Morningglory                                                                             90        95     90     90   85                                      Rape      95        100    95     65   100                                     Redroot Pigweed                                                                          100       65     100    100  100                                     Rice Japonica                                                                            85        65     55     35   70                                      Soybean   60        75     50     75   75                                      Speedwell 100       85     100    --   100                                     Sugar beet                                                                               100       100    100    85   100                                     Umbrella sedge                                                                           75        20      0     75   80                                      Velvetleaf                                                                               100       90     100    100  100                                     Watergrass 2                                                                             100       85     65     50   80                                      Wheat     60        25     45     90   45                                      Wild buckwheat                                                                           100       90     100    80   100                                     Wild oat  40        35     20     80   30                                      2 Leaf BYG                                                                               100       60     50     30   80                                      PREEMERGENCE                                                                   Barley Igri                                                                              35         0      0      0    0                                      Barnyardgrass                                                                            85        75     75     65   85                                      Blackgrass                                                                               95        20      0     45   50                                      Chickweed 40         0      0      0   65                                      Cocklebur  0         0     10     25   20                                      Corn      35         0     20     35   60                                      Cotton    25         0      0     35    0                                      Crabgrass 90        55     40     100  95                                      Downy Brome                                                                              60         0     30     10    0                                      Galium    35         0      0      0   50                                      Giant foxtail                                                                            100       85     15     100  70                                      Italn. Rygrass                                                                           95        20     20     45   80                                      Johnsongrass                                                                             100       55     95     95   85                                      Lambsquarters                                                                            100       90     90     100  100                                     Morningglory                                                                             40         0      0      0   65                                      Rape      100        0      0     45   35                                      Redroot Pigweed                                                                          100       100    75     100  100                                     Soybean   60        10     30     25   65                                      Speedwell 100        0     30     100  100                                     Sugar beet                                                                               90         0     45     100  80                                      Velvetleaf                                                                               100       100    100    100  100                                     Wheat     50         0      0      0    0                                      Wild buckwheat                                                                           95         0     35     90   75                                      Wild oat  75         0      0     35   30                                      ______________________________________                                                 COMPOUND                                                               Rate 16 g/ha                                                                             11        12     14     20   22                                      ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri                                                                              45        25     35     50    0                                      Barnyardgrass                                                                            70         0     35      0   40                                      Blackgrass                                                                               35        30     25     25   50                                      Chickweed 45        20     20     20   80                                      Cocklebur  0        40     35     --   50                                      Corn       0        25     20     35   10                                      Cotton    65        100    80     100  95                                      Crabgrass  0        30     25     45   10                                      Downy Brome                                                                              60        40     30     25   30                                      Duck salad                                                                                0         0      0      0    0                                      Galium    --        45     45      0    0                                      Giant foxtail                                                                            20        20     40     50   45                                      Italn. Rygrass                                                                           80        30     45     40   25                                      Johnsongrass                                                                             20        70     85     50   90                                      Lambsquarters                                                                            100       90     95     95   100                                     Morningglory                                                                             80        65     90     85   85                                      Rape      80        100    85     50   100                                     Redroot Pigweed                                                                          85        50     85     --   20                                      Rice Japonica                                                                            70        55     35     35   20                                      Soybean   55        75     45     55   75                                      Speedwell 100       85     100    --   100                                     Sugar beet                                                                               100       100    100    40   100                                     Umbrella sedge                                                                           70         0      0     65   70                                      Velvetleaf                                                                               90        85     100    100  100                                     Watergrass 2                                                                             70        30      0     35   65                                      Wheat     55        25     35     50   30                                      Wild buckwheat                                                                           95        90     70     35   100                                     Wild oat  30        30     10     65   25                                      2 Leaf BYG                                                                               80        40     25     20   60                                      PREEMERGENCE                                                                   Barley Igri                                                                              35         0      0      0    0                                      Barnyardgrass                                                                            65         0      0     65   30                                      Blackgrass                                                                               95         0      0     25   40                                      Chickweed  0         0      0      0   40                                      Cocklebur  0         0      0      0    0                                      Corn      20         0      0      0    0                                      Cotton    25         0      0     10    0                                      Crabgrass 85        50     40     60   95                                      Downy Brome                                                                              50         0     30     10    0                                      Galium     0         0      0      0    0                                      Giant foxtail                                                                            95         0     10     50   70                                      Italn. Rygrass                                                                           85         0      0     35   10                                      Johnsongrass                                                                             95        30     35     90   75                                      Lambsquarters                                                                            100       70     80     100  100                                     Morningglory                                                                             35         0      0      0   65                                      Rape      100        0      0     25    0                                      Redroot Pigweed                                                                          100       70     45     100  100                                     Soybean   30         0      0     10   40                                      Speedwell 100        0      0      0   90                                      Sugar beet                                                                               --         0      0     95   80                                      Velvetleaf                                                                               100       40     100     0   100                                     Wheat     30         0      0      0    0                                      Wild buckwheat                                                                           75         0     30     80   60                                      Wild oat  40         0      0     35   15                                      ______________________________________                                                   COMPOUND                                                             Rate 8 g/ha                                                                              22                                                                   ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri                                                                               0                                                                   Barnyardgrass                                                                            35                                                                   Blackgrass                                                                               35                                                                   Chickweed 70                                                                   Cocklebur 35                                                                   Corn      10                                                                   Cotton    95                                                                   Crabgrass  0                                                                   Downy Brome                                                                              30                                                                   Duck salad                                                                                0                                                                   Galium     0                                                                   Giant foxtail                                                                            30                                                                   Italn. Rygrass                                                                            0                                                                   Johnsongrass                                                                             75                                                                   Lambsquarters                                                                            95                                                                   Morningglory                                                                             85                                                                   Rape      85                                                                   Redroot Pigweed                                                                          10                                                                   Rice Japonica                                                                             5                                                                   Soybean   65                                                                   Speedwell 40                                                                   Sugar beet                                                                               80                                                                   Umbrella sedge                                                                           10                                                                   Velvetleaf                                                                               100                                                                  Watergrass 2                                                                             20                                                                   Wheat     30                                                                   Wild buckwheat                                                                           75                                                                   Wild oat  20                                                                   2 Leaf BYG                                                                               10                                                                   PREEMERGENCE                                                                   Barley Igri                                                                               0                                                                   Barnyardgrass                                                                            10                                                                   Blackgrass                                                                                0                                                                   Chickweed  0                                                                   Cocklebur  0                                                                   Corn       0                                                                   Cotton     0                                                                   Crabgrass 95                                                                   Downy Brome                                                                               0                                                                   Galium     0                                                                   Giant foxtail                                                                            55                                                                   Italn. Rygrass                                                                            0                                                                   Johnsongrass                                                                             50                                                                   Lambsquarters                                                                            95                                                                   Morningglory                                                                             60                                                                   Rape       0                                                                   Redroot Pigweed                                                                          90                                                                   Soybean   10                                                                   Speedwell  0                                                                   Sugar beet                                                                               35                                                                   Velvetleaf                                                                               65                                                                   Wheat      0                                                                   Wild buckwheat                                                                           45                                                                   Wild oat   0                                                                   ______________________________________                                    

TEST D

Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Convolvolus erubescens), black nightshade (Solanum ptycanthum dunal), cassia (Cassia unifloria), cocklebur (Xanthium pensylvanicum), common ragweed (Ambrosia artemisiifolia), corn (Zea mays), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum (Panicum dichotomifiorum), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnson grass (Sorghum halepense), lambsquarter (Chenpopdium album), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), prickly sida (Sida spinosa), shattercane (Sorghum vulgare), signalgrass (Brachiaria platyphylla), smartweed (Polygonum persicaria), soybean (Glycine max), sunflower (Helianthus annuus), velvetleaf (Abutilon theophrasti), wild proso (Pancium miliaceum), wooly cup grass (Eriochloa villosa), yellow foxtail (Setaria lutescens) and purple nutsedge (Cyperus rotundus) tubers were planted into a matapeake sandy loam soil. These crops and weeds were grown in the greenhouse until the plants ranged in height from two to eighteen cm (one to four leaf stage), then treated postemergence with the test chemicals dissolved in a non-phytotoxic solvent. Pots receiving these postemergence treatments were placed in the greenhouse and maintained according to routine greenhouse procedures. Treated plants and untreated controls were maintained in the greenhouse approximately 14-21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table D, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control.

                  TABLE D                                                          ______________________________________                                         PREEMERGENCE                                                                                  COMPOUND                                                        Rate 280 g/ha  12                                                              ______________________________________                                         Barnyardgrass  100                                                             Bindweed       100                                                             Blk Nightshade 100                                                             Cassia         70                                                              Cocklebur      55                                                              Corn           80                                                              Cotton         90                                                              Crabgrass      100                                                             Fall Panicum   100                                                             Giant Foxtail  100                                                             Green Foxtail  100                                                             Jimson Weed    100                                                             Johnson Grass  100                                                             Lambsquarter   100                                                             Morningglory   100                                                             Nustedge       25                                                              Pigweed        100                                                             Prickly Sida   100                                                             Ragweed        90                                                              Shattercane    95                                                              Signalgrass    100                                                             Smartweed      100                                                             Soybean        100                                                             Sunflower      80                                                              Velvetleaf     100                                                             Wild Proso     100                                                             Wolly Cup Grass                                                                               95                                                              Yellow Foxtail 100                                                             ______________________________________                                                        COMPOUND                                                        Rate 17.5 g/ha 12                                                              ______________________________________                                         Barnyardgrass  65                                                              Bindweed        0                                                              Blk Nightshade  0                                                              Cassia         100                                                             Cocklebur       0                                                              Corn            0                                                              Cotton          0                                                              Crabgrass      60                                                              Fall Panicum   65                                                              Giant Foxtail  60                                                              Green Foxtail  55                                                              Jimson Weed    15                                                              Johnson Grass  80                                                              Lambsquarter   100                                                             Morningglory    0                                                              Nustedge        0                                                              Pigweed        65                                                              Prickly Sida   50                                                              Ragweed        15                                                              Shattercane    15                                                              Signalgrass    20                                                              Smartweed      70                                                              Soybean         0                                                              Sunflower       0                                                              Velvetleaf     50                                                              Wild Proso     20                                                              Wolly Cup Grass                                                                               10                                                              Yellow Foxtail 55                                                              ______________________________________                                                        COMPOUND                                                        Rate 140 g/ha  12                                                              ______________________________________                                         Barnyardgrass  100                                                             Bindweed       100                                                             Blk Nightshade 100                                                             Cassia         50                                                              Cocklebur      25                                                              Corn           70                                                              Cotton         65                                                              Crabgrass      100                                                             Fall Panicum   100                                                             Giant Foxtail  100                                                             Green Foxtail  100                                                             Jimson Weed    100                                                             Johnson Grass  100                                                             Lambsquarter   100                                                             Morningglory   45                                                              Nustedge       15                                                              Pigweed        100                                                             Prickly Sida   100                                                             Ragweed        90                                                              Shattercane    80                                                              Signalgrass    90                                                              Smartweed      100                                                             Soybean        65                                                              Sunflower      65                                                              Velvetleaf     100                                                             Wild Proso     100                                                             Wolly Cup Grass                                                                               80                                                              Yellow Foxtail 90                                                              ______________________________________                                                        COMPOUND                                                        Rate 70 g/ha   12                                                              ______________________________________                                         Barnyardgrass  95                                                              Bindweed       100                                                             Blk Nightshade 100                                                             Cassia         30                                                              Cocklebur      15                                                              Corn           55                                                              Cotton         15                                                              Crabgrass      100                                                             Fall Panicum   100                                                             Giant Foxtail  100                                                             Green Foxtail  100                                                             Jimson Weed    70                                                              Johnson Grass  100                                                             Lambsquarter   100                                                             Morningglory   30                                                              Nustedge        0                                                              Pigweed        100                                                             Prickly Sida   100                                                             Ragweed        50                                                              Shattercane    60                                                              Signalgrass    90                                                              Smartweed      100                                                             Soybean        15                                                              Sunflower      25                                                              Velvetleaf     100                                                             Wild Proso     80                                                              Wolly Cup Grass                                                                               65                                                              Yellow Foxtail 85                                                              ______________________________________                                                        COMPOUND                                                        Rate 35 g/ha   12                                                              ______________________________________                                         Barnyardgrass  75                                                              Bindweed       15                                                              Blk Nightshade 100                                                             Cassia          0                                                              Cocklebur       0                                                              Corn           25                                                              Cotton          0                                                              Crabgrass      65                                                              Fall Panicum   100                                                             Giant Foxtail  75                                                              Green Foxtail  75                                                              Jimson Weed    55                                                              Johnson Grass  85                                                              Lambsquarter   100                                                             Morningglory    0                                                              Nustedge        0                                                              Pigweed        80                                                              Prickly Sida   65                                                              Ragweed        50                                                              Shattercane    15                                                              Signalgrass    60                                                              Smartweed      95                                                              Soybean         0                                                              Sunflower      15                                                              Velvetleaf     70                                                              Wild Proso     40                                                              Wolly Cup Grass                                                                               10                                                              Yellow Foxtail 65                                                              ______________________________________                                    

TEST E

Seeds, rhizomes, or plant parts of alfalfa (Medicago sativa), annual bluegrass (Poa annua), bermudagrass (Cynodon dactylon), broadleaf signalgrass (Brachiaria platyphylia), common purslane (Portulaca oleracea), common ragweed (Ambrosia artemisiifolia), dallisgrass (Paspalum dilatatum), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia cochinchinensis), johnsongrass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), peanut (Arachis hypoagaea), pitted momingglory (Ipomoea lacunosa), purple nutsedge (Cyperus rotundus), sandbur (Southern sandbur), smooth crabgrass (Digitaria ischaemum) were planted into greenhouse pots containing greenhouse planting medium. Each pot contained only one plant species.

The test compound was dissolved in a non-phytotoxic solvent and applied preemergence and/or postemergence to the plants. Preemergence applications were made within one day of planting the seeds or plant parts. Postemergence applications were applied when the plants were in the two to four leaf stage (three to twenty cm). Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury at 14 to 28 days after herbicide application. Plant response ratings, summarized in Table E, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) response indicates no test result.

                  TABLE 3                                                          ______________________________________                                                      COMPOUND                                                          Rate 0500 g/ha                                                                              11                                                                ______________________________________                                         POSTEMERGENCE                                                                  Alfalfa Var. 100                                                               Ann Bluegrass                                                                               100                                                               Bermudagrass 100                                                               Brdlf Sgnlgrass                                                                             100                                                               Cmn Purslane 100                                                               Cmn Ragweed  100                                                               Dallisgrass  100                                                               Goosegrass   100                                                               Guineagrass  100                                                               Itchgrass    100                                                               Johnsongrass 98                                                                Large Crabgrass                                                                             95                                                                Peanuts      95                                                                Pit Morninglory                                                                             70                                                                Purple Nustedge                                                                             75                                                                S. Sandbur   100                                                               Smooth Crabgras                                                                             90                                                                PREEMERGENCE                                                                   Alfalfa Var. 100                                                               Ann Bluegrass                                                                               100                                                               Bermudagrass 100                                                               Brdlf Sgnlgrass                                                                             100                                                               Cmn Purslane 100                                                               Cmn Ragweed  100                                                               Dallisgrass  100                                                               Goosegrass   100                                                               Guineagrass  100                                                               Itchgrass    98                                                                Johnsongrass 100                                                               Large Crabgrass                                                                             100                                                               Peanuts      60                                                                Pit Morninglory                                                                             10                                                                Purple Nustedge                                                                             90                                                                S. Sandbur   100                                                               Smooth Crabgras                                                                             100                                                               ______________________________________                                                    COMPOUND                                                            Rate 0250 g/ha                                                                              1           8      11                                             ______________________________________                                         Alfalfa Var.  0          20     98                                             Ann Bluegrass                                                                                0          50     95                                             Bermudagrass  0          40     98                                             Brdlf Sgnlgrass                                                                              0          70     100                                            Cmn Purslane 30          50     100                                            Cmn Ragweed  --          --     100                                            Dallisgrass   0           0     100                                            Goosegrass   20          40     90                                             Guineagrass   0          90     75                                             Itchgrass     0          60     95                                             Johnsongrass  0          70     100                                            Large Crabgrass                                                                              0          50     80                                             Peanuts       0          60     98                                             Pit Morninglory                                                                              0          70     75                                             Purple Nustedge                                                                              0          40     80                                             S. Sandbur   --          50     95                                             Smooth Crabgras                                                                              0          70     75                                             PREEMERGENCE                                                                   Alfalfa Var. 30          100    100                                            Ann Bluegrass                                                                                0          80     100                                            Bermudagrass 20          100    100                                            Brdlf Sgnlgrass                                                                              0          100    100                                            Cmn Purslane  0          100    100                                            Cmn Ragweed  --          --     100                                            Dallisgrass  40          100    100                                            Goosegrass   50          100    100                                            Guineagrass  80          100    100                                            Itchgrass     0          90     100                                            Johnsongrass  0          100    100                                            Large Crabgrass                                                                             60          100    100                                            Peanuts       0          20     60                                             Pit Morninglory                                                                              0           0     100                                            Purple Nustedge                                                                              0           0     80                                             S. Sandbur   50          100    100                                            Smooth Crabgras                                                                             30          100    100                                            ______________________________________                                                    COMPOUND                                                            Rate 0125 g/ha                                                                              8           11     34                                             ______________________________________                                         POSTEMERGENCE                                                                  Alfalfa Var.  0          50     20                                             Ann Bluegrass                                                                                0          65     20                                             Bermudagrass  0          98     60                                             Brdlf Sgnlgrass                                                                             50          20     10                                             Cmn Purslane 50          80     10                                             Cmn Ragweed  --          95     --                                             Dallisgrass   0          65      0                                             Goosegrass   20          50     10                                             Guineagrass  70          20      0                                             Itchgrass    60          40      0                                             Johnsongrass 20          40     10                                             Large Crabgrass                                                                              0          30      0                                             Peanuts      30          60     30                                             Pit Morninglory                                                                             30          20     90                                             Purple Nustedge                                                                             --          20     60                                             S. Sandbur   30          30      0                                             Smooth Crabgras                                                                             30          15      0                                             PREEMERGENCE                                                                   Alfalfa Var. 30          100    60                                             Ann Bluegrass                                                                               80          90      0                                             Bermudagrass 100         90     100                                            Brdlf Sgnlgrass                                                                             80          100    40                                             Cmn Purslane 100         100    100                                            Cmn Ragweed  --          100    --                                             Dallisgrass  100         100    80                                             Goosegrass   100         100    100                                            Guineagrass  100         100    100                                            Itchgrass    90          80     20                                             Johnsongrass 100         100    30                                             Large Crabgrass                                                                             100         100    80                                             Peanuts      20          10      0                                             Pit Morninglory                                                                              0          10     50                                             Purple Nustedge                                                                              0          20      0                                             S. Sandbur   100         90     60                                             Smooth Crabgras                                                                             100         90     80                                             ______________________________________                                     

What is claimed is:
 1. A compound of Formula I: ##STR25## wherein the left-hand ring contains only single bonds or one bond in the ring is a double bond;n is 2; R¹ is selected from the group H, halogen; hydroxy, C₁ -C₃ alkoxy; C₁ -C₃ haloalkoxy; C₂ -C₅ alkylcarbonyloxy; or C₂ -C₅ haloalkylcarbonyloxy; R² is selected from the group H, hydroxy, and halogen; or when R¹ and R² are bonded to the same carbon atom they can be taken together along with the carbon to which they are attached to form C═O; or when R¹ and R² are bonded to adjacent carbon atoms they can be taken together along with the carbons to which they are attached to form ##STR26## Q is selected from the group ##STR27## R³ is selected from the group H and halogen; R⁴ is selected from the group H, C₁ -C₈ alkyl, C₁ -C₈ haloalkyl, halogen, OR⁹, S(O)_(m) R⁹, COR⁹, CO₂ R⁹, C(O)SR⁹, C(O)NR¹¹ R¹², CHO, CR⁷ ═CR⁷ CO₂ R⁹, CO₂ N═CR¹³ R¹⁴, NO₂, CN, NHSO₂ R¹⁵ and NHSO₂ NHR¹⁵ ; m is 0, 1 or 2; R⁵ is selected from the group C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, OCH₃, SCH₃, OCHF₂, halogen, CN and NO₂ ; R⁶ is selected from the group H, C₁ -C₃ alkyl, C₂ -C₃ alkynyl, C₂ -C₃ haloalkynyl, CO₂ (C₁ -C₄ alkyl), and halogen; R⁷ is independently selected from the group H, C₁ -C₃ alkyl and halogen; or when Q is Q-2 or Q-6, R⁶ and R⁷ together with the carbon to which they are attached can be C═O; R⁹ is selected from the group C₁ -C₈ alkyl; C₃ -C₈ cycloalkyl; C₃ -C₈ alkenyl; C₃ -C₈ alkynyl; C₁ -C₈ haloalkyl; C₂ -C₈ alkoxyalkyl; C₂ -C₈ alkylthioalkyl; C₂ -C₈ alkylsulfinylalkyl; C₂ -C₈ alkylsulfonylalkyl; C₁ -C₈ alkylsulfonyl; phenylsulfonyl optionally substituted on the phenyl ring with halogen or C₁ -C₄ alkyl; C₄ -C₈ alkoxyalkoxyalkyl, C₄ -C₈ cycloalkylalkyl; C₄ -C₈ alkenoxyalkyl; C₄ -C₈ alkynoxyalkyl; C₆ -C₈ cycloalkoxyalkyl; C₄ -C₈ alkenyloxyalkyl; C₄ -C₈ alkynyloxyalkyl; C₃ -C₈ haloalkoxyalkyl; C₄ -C₈ haloalkenoxyalkyl; C₄ -C₈ haloalkynoxyalkyl; C₆ -C₈ cycloalkylthioalkyl; C₄ -C₈ alkenylthioalkyl; C₄ -C₈ alkynylthioalkyl; C₁ -C₄ alkyl substituted a substituent selected from phenoxy and benzyloxy, each ring optionally substituted with a substituent selected from halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; C₄ -C₈ trialkylsilylalkyl; C₃ -C₈ cyanoalkyl; C₃ -C₈ halocycloalkyl; C₃ -C₈ haloalkenyl; C₅ -C₈ alkoxyalkenyl; C₅ -C₈ haloalkoxyalkenyl; C₅ -C₈ alkylthioalkenyl; C₃ -C₈ haloalkynyl; C₅ -C₈ alkoxyalkynyl; C₅ -C₈ haloalkoxyalkynyl; C₅ -C₈ alkylthioalkynyl; C₂ -C₈ alkyl carbonyl; benzyl optionally substituted with a substituent selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; CHR¹⁶ COR¹⁰ ; CHR¹⁶ CO₂ R¹⁰ ; CHR¹⁶ P(O)(OR¹⁰)₂ ; CHR¹⁶ P(S)(OR¹⁰)₂ ; CHR¹⁶ C(O)NR¹¹ R¹² ; and CHR¹⁶ C(O)NH₂ ; R¹⁰ is selected from the group C₁ -C₆ alkyl, C₁ -C₆ alkenyl and C₁ -C₆ alkynyl; R¹¹ and R¹³ are independently selected from the group H and C₁ -C₄ alkyl; R¹² and R¹⁴ are independently selected from the group C₁ -C₄ alkyl and phenyl optionally substituted with a substituent selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; R¹³ and R¹⁴ may be taken together with the carbon to which they are attached to form C₃ -C₈ cycloalkyl; R¹⁵ is selected from the group C₁ -C₄ alkyl and C₁ -C₄ haloalkyl; R¹⁶ is selected from the group H and C₁ -C₃ alkyl; and W is selected from the group O and S;provided that R¹ is other than H when the left-hand ring contains only single bonds.
 2. A of claim 1 wherein:R¹ is halogen; R ² is selected from the group H, and halogen; Q is selected from the group consisting of Q-1 and Q-2 R³ is halogen; R⁵ is selected from the group C₁ -C₂ haloalkyl, OCH₃, OCHF₂, CN, NO₂, and halogen; R⁶ is selected from the group H, C₁ -C₃ alkyl, C₂ -C₃ alkynyl, C₂ -C₃ haloalkynyl, and halogen; R⁷ is H; and W is O.
 3. A compound of claim 2 wherein:R⁴ is selected from the group halogen, OR⁹, S(O)_(m) R⁹, COR⁹, CO₂ R⁹, C(O)NR¹¹ R₂, CH═CHCO₂ R⁹, NHSO₂ R¹⁵ and NHSO₂ NHR¹⁵ ; R⁵ is halogen; R⁶ is selected from the group H and C₁ -C₃ alkyl; R⁷ is H; and R⁹ is selected from the group C₁ -C₈ alkyl; C₃ -C₈ cycloalkyl; C₃ -C₈ alkenyl; C₃ -C₈ alkynyl; C₁ -C₈ haloalkyl; C₂ -C₈ alkoxyalkyl; C₁ -C₄ alkyl substituted with a substituent selected from phenoxy and benzyloxy, each ring optionally substituted with a substituent selected from halogen, C₁ -C₃ alkyl and C₁ -₃ haloalkyl; C₃ -C₈ haloalkenyl; C₃ -C₈ haloalkynyl; C₂ -C₈ alkyl carbonyl; benzyl optionally substituted with a substituent selected from the group halogen, C₁ -C₃ alkyl and C₁ -C₃ haloalkyl; CHR¹⁶ COR¹⁰ ; CHR¹⁶ CO₂ R¹⁰ ; CHR¹⁶ P(O)(OR¹⁰)₂ ; CHR¹⁶ C(O)NR¹¹ R¹² ; and CHR¹⁶ C(O)NH₂.
 4. The compound of claim 3 which is: 2,5,6,7-tetrahydro-2- 2,4-dichloro-5-(2-propynyloxy)phenyl!-6-fluoro-3H-pyrrolo 2,1-c!-1,2,4triazol-3-one; and! 5,6,7,8-tetrahydro-2-8- 2,4-dichloro-5-(2propynyloxy)phenyl!-8chloro-1,2,4-triazolo 4,3-α pyridin-3(2H)-one.
 5. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 1 and at least one of a surfactant, solid or liquid diluent.
 6. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 2 and at least one of a surfactant, solid or liquid diluent.
 7. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 3 and at least one of a surfactant, solid or liquid diluent.
 8. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 4 and at least one of a surfactant, solid or liquid diluent.
 9. A method for controlling the growth of undesired vegetation comprising applying to the locus to be protected an effective amount of the composition of claim
 5. 10. A method for controlling the growth of undesired vegetation comprising applying to the locus to be protected an effective amount of a composition of claim
 8. 